Styryl carboxylate derivatives

ABSTRACT

Novel Styryl Carboxylate derivatives are provided which exhibit activity for the treatment of immunological diseases, inflammation, obesity, hyperlipidemia, hypertension, neurological diseases, and diabetes.

RELATIONSHIP TO OTHER APPLICATIONS

This patent claims the benefit of the earlier filing date of U.S. Provisional Application No. 63/141,816 filed 26 Jan. 2021, which is incorporated herein by reference.

FIELD OF THE INVENTION

The present invention relates to novel styryl carboxylates for the treatment of immunological diseases, inflammation, obesity, hyperlipidaemia, hypertension, neurological diseases, and diabetes.

BACKGROUND OF THE INVENTION

Metabolic syndrome, Insulin resistance syndrome or Syndrome X is a name for a group of risk factors that occur together and increase the risk for coronary artery disease, stroke, and type 2 diabetes. Metabolic syndrome is becoming more and more common globally specially in the United States. Researchers are not sure whether the syndrome is due to one single cause, but all the risks for the syndrome are related to obesity. The two most important risk factors for metabolic syndrome are: Extra weight around the middle and upper parts of the body (central obesity) and insulin resistance. The body uses insulin less effectively than normal. Insulin is needed to help control the amount of sugar in the body. As a result, blood sugar and fat levels rise. Other risk factors include Aging, Genes, Hormone changes, Lack of exercise. People who have metabolic syndrome often have two other problems that can either cause the condition or make it worse. Excess blood clotting, and increased levels of blood substances that are a sign of inflammation throughout the body

Metabolic syndrome is affiliated with three or more of the following signs: Blood pressure equal to or higher than 130/85 mmHg, Fasting blood sugar (glucose) equal to or higher than 100 mg/dL, large waist circumference (length around the waist Men—40 inches or more and Women—35 inches or more, Low HDL cholesterol (Men—under 40 mg/dL Women—under 50 mg/dL) and Triglycerides equal to or higher than 150 mg/dL. In general, metabolic syndrome is a combination of Type 2 diabetes, obesity, hyperlipidemia and hypertension

People with metabolic syndrome have an increased long-term risk for developing heart disease, type 2 diabetes, stroke, kidney disease, and poor blood supply to the legs. There is no one single treatment option available to treat metabolic syndrome. Current drugs that control blood glucose are usually not effective in lowering body weight, hypertension and cholesterol. Similarly, drugs that manage lipid levels may or may not have impact on other metabolic parameters. The present invention was aimed to develop new class of therapeutics derived, modified, and chemically synthesized from natural product which can combat multiple arms of metabolic syndrome. The invention also describes one such core group of molecules with synthesis scheme and biological data for diabetes, obesity, inflammation, hypertension and hyperlipidemia.

The compounds and compositions of the present invention are used to treat diseases associated with Inflammation, which include (but are not limited to) the following: Chron's Disease, Appendicitis, Bursitis, Colitis, Cystitis, Dermatitis, Epididymitis, Gingivitis, Meningitis, Myelitis, Nephritis, Neuritis, Pancreatitis, Periodontitis, Pharyngitis, Phlebitis, Prostatitis, Sinusitis, Tendonitis, Tonsillitis, Urethritis, Vasculitis, Vaginitis, Rheumatoid Arthritis, Osteoarthritis, Psoriatic Arthritis, Septic Arthritis, Chronic Inflammation, Asthma, Hepatitis, Laryngitis, Thyroiditis, Lymphangitis, Gout, Arteritis, Bronchitis, Acne Vulgaris, Pneumonia, Sarcoidosis, Endocarditis, Myocarditis, Pericarditis, Duodenitis, Esophagitis, Folliculitis, Anemia, Hypersensitivity, Chronic Obstructive Pulmonary Disease, Complex Regional Pain Syndrome, Rhinitis and Celiac Disease.

The compounds and compositions of the present invention are used to treat diseases associated with Metabolic Syndrome, which include (but are not limited to) the following: Obesity, Dyslipidemia, Hyperglycemia, Non Alcoholic Fatty Liver Disease, Polycystic Ovary Syndrome, Sleep Apnea, Hyperinsulinemia, Insulin Resistance, Glucose Intolerance, Hypertension, Acanthosis Nigricans, Psoriasis, Coronary Artery Disease, Cardiac Arrest, Congestive Heart Failure, Arrhythmia, Peripheral Artery Disease, Stroke, Ischemic Heart Disease, Lipodystrophy, Diabetes Mellitus Type 2, Kidney Failure, Low Levels of HDL and Chronic Inflammation.

SUMMARY OF THE INVENTION

The present invention relates to novel Styryl Carboxylate derivatives of the formula (I)

their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates, wherein R₁, R₂, R₃, R₄ and R₅ represent substituents on ring A and R₆, R₇ and R₈ along with X and Y represent substituents on ring B as indicated in formula (I).

The present invention also relates to a process for the preparation of the above said novel compounds, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates, novel intermediates and pharmaceutical compositions containing them. Tautomeric forms are isomeric forms which exists in a state of equilibrium capable of reacting according to either form. Stereoisomers include configurational isomers, such as cis- and trans double bonds, as well as optically active isomers having different spatial arrangements of their atoms. Polymorphs are molecules which can crystallize in two or more forms. Solvates are molecular or ionic complexes of molecules or ions of solvent with those of a solute. Analogs also include atoms of the same family of the Periodic Table, such as F, Cl, Br and I. Derivatives include compounds resulting from routine functionalizing of atoms, such as, derivatives found by protecting by carboxylation or esterification, respectively.

BRIEF DESCRIPTION OF FIGURES

FIG. 1A shows that mice treated with compound 1 showed a significant decrease (P<0.0001) by 16% in body weight compared with the Control high fat diet group. FIG. 1B shows that mice treated with compound 1 showed a significant decrease (P<0.0001) by 54% in percent body weight compared with the Control high fat diet group.

FIG. 2 shows that mice treated with compound 1 showed 15% reduction in fasting blood glucose compared with the control group high fat diet group.

FIG. 3A shows that group of mice treated with compound 1 showed a significant reduction (P<0.002) by 27% in fasting blood glucose compared with the group of mice maintained on high fat diet. FIG. 3B shows the effect of compound 1 on oral glucose tolerance test at Day 90 when compared with the control group of mice on high fat diet. FIG. 3C shows that the group of mice treated with compound 1 showed a significant decrease (P<0.009) by 28% in blood glucose compared at the peak oral glucose tolerance test of 30 minutes compared with the Control high fat diet group.

FIG. 4 shows that mice treated with compound 1 showed a 14% decrease in Total Cholesterol and a significant decrease (P<0.01) by 35% in Triglyceride, compared with the Control high fat diet group.

FIG. 5A shows that at the end of the drug treatment period, the group of mice treated with compound 1 showed a significant (P<0.0001) decrease in body weight by 19%, compared with the high fat diet group. FIG. 5B shows that at the end of the drug treatment period, the group of mice treated with compound 1 showed a 17% decrease in body weight when compared with the control high fat diet group.

FIG. 6A shows the effect of compound 1 on oral glucose tolerance test FIG. 6B shows that the group of mice treated with compound 1 showed 7% lower fasting blood glucose compared with the Control high fat diet group of mice. FIG. 6B shows that at the end of 120 minutes in the oral glucose tolerance test, the group of mice administered with compound 1 showed a 7% decrease in blood glucose compared with the Control high fat diet group.

FIG. 7 shows that mice treated with compound 1 showed significant reduction (P<0.0001) by 24% in body weight compared with the untreated group of mice starting from day 6 till the entire duration of the study.

FIG. 8 shows that mice treated with compound 1 showed significant reduction (P<0.003) by 34% in blood glucose compared with the untreated group of mice starting from day 6 till the entire duration of the study.

FIG. 9A shows that at the end of the study duration of 30 days, mice treated with compound 1 showed significant reduction (P<0.003) by 34% in blood glucose compared with the untreated group of mice starting from day 6 till the entire duration of the study. FIG. 9B shows that mice treated with compound 1 showed significant reduction by 32% in blood glucose compared with the untreated group of mice.

FIG. 10A shows that the group of mice administered with compound 1 showed a 24% decrease in Total Cholesterol on day 90 and 34% decrease in Total Cholesterol on day 180 from the control high fat diet group. FIG. 10B shows that the group of mice administered with compound 1 showed a 52% increase on day 90 and 62% increase on day 180 in high density lipoprotein (HDL) from the control high fat diet group. FIG. 10C shows that the group of mice administered with compound 1 showed a 32% decrease in low density lipoprotein (LDL) on day 90 from the control high fat diet group. FIG. 10D shows that the group of mice administered with compound 1 showed a 7% decrease on day 90 and 26% decrease on day 180 in Triglycerides from the control high fat diet group. FIG. 10E shows that the group of mice administered with compound 1 showed a 35% decrease on day 90 and 39% decrease on day 180 in blood glucose from the control high fat diet group.

FIG. 11A shows that the group of rats treated with compound 1 showed a significant (P<0.002) decrease by 11% in fasting blood glucose than the vehicle group of rats on day 30 and

FIG. 11B shows a decrease by 9% on day 60, compared with the Control group of rats.

FIG. 12 shows that rats treated with compound 1 showed 10% decrease in systolic blood pressure and a 9% decrease in diastolic blood pressure, compared with the control group of rats.

FIG. 13 shows that rats administered with compound 1 showed a 31% decrease in HOMA IR from the group of Control rats.

FIG. 14A shows that the group of hamsters administered with compound 1 showed a significant (P<0.03) reduction by 19% blood glucose, compared with the Control group of high fructose fed hamsters. Triglycerides were then measured in the plasma of the fasted hamsters. FIG. 14 B shows that the group of hamsters treated with compound 1 showed a significant (p<0.0002) decrease by 55% in Triglycerides, compared with the Control group of high fructose fed hamsters.

FIG. 15 shows that hamsters administered with compound 1 showed a 39% decrease in Total Cholesterol (FIG. 15A), a 35% increase in high-density lipoproteins (HDL) (FIG. 15B), a 34% decrease in low-density lipoproteins (LDL) (FIG. 15C), a 50% decrease in Triglycerides (FIG. 15D) and a 13% decrease in blood glucose (FIG. 15E) compared with the Control high cholesterol group.

FIG. 16 shows hamsters treated with compound 1 showed a decrease by 20% in Total Cholesterol compared with the high cholesterol fed group.

FIG. 17 shows that mice administered with compound 1 showed 66% decreases of TNF-α from the LPS group.

FIG. 18A shows the body weight of mice administered with compound 1 compared to the control high fat with sucrose group. FIG. 18B shows that mice administered with compound 1 showed a significant (P<0.0001) decrease by 20% in body weight from the control high fat with sucrose group.

FIG. 19 shows that the group of mice administered with compound 1 showed a significant (P<0.04) decrease by 18% in fasting blood glucose from the control high fat with sucrose group.

FIG. 20 shows that mice administered with compound 1 showed a significant (P<0.009) decrease by 25% in fasting blood glucose from the control high fat with sucrose group (FIG. 21A). An oral glucose tolerance test was conducted. For this test the mice were administered with glucose orally at 2 g/Kg. Blood glucose was measured at the fasted state (baseline, taken prior to glucose administration), then at 30, 60, 90 and 120 minutes (FIG. 20B). The group of mice treated with compound 1 showed significant (P<0.004) decrease by 28% in blood glucose at the peak time of 30 minutes (FIG. 20C).

FIG. 21 shows that mice administered with compound 1 showed a 19% decrease in liver weight compared with the high fat with sucrose group.

FIG. 22 shows that mice administered with compound 1 showed a 22% decrease in abdominal fat weight compared with the high fat with sucrose group.

FIGS. 23A and B shows that Mice treated with compound 5 showed an 110% decrease in body weight compared with the Control high fat diet group.

FIG. 24A shows that the group of mice administered with compound 5 showed an 8% decrease in fasting blood glucose, compared with the control high fat diet group. FIG. 24B shows the effect of compounds 2, 3, 4, and 5 on oral glucose tolerance test at 60 days. The group of mice treated with compound 5 showed significant (P<0.03) decrease by 32% in blood glucose at the peak time of 30 minutes compared with the control high fat diet group in the oral glucose tolerance test (FIG. 24C).

FIG. 25A shows the effect of compound 2, 3, 4, and 5 on fasting blood glucose at Day 90. FIG. 25B shows the effect of compound 2, 3, 4, and 5 on oral glucose tolerance test at Day 90. FIG. 25C shows that mice treated with compound 5 showed a decrease by 19% in blood glucose at the peak time of 30 minutes in the oral glucose tolerance test when compared with the control high fat diet group.

FIG. 26 shows that mice treated with compound 6 showed 10% reduction in fasting blood glucose on day 60 (FIG. 26A) and an 11% decrease on day 90 (FIG. 26B), compared with the control high fat diet group.

FIG. 27 shows that mice treated with compound 7 showed 7% reduction in fasting blood glucose on day 60 compared with the control high fat diet group.

FIG. 28A shows that compound 6 showed a significant (P<0.0001) decrease by 5% in body weight compared with the control group. FIG. 28B shows that at the end of 90 days, the group of mice treated with compound 6 showed a significant (P<0.0001) decrease by 15% in body weight compared with the Control high fat diet group.

FIG. 29A shows the effect of compound 8 on oral glucose tolerance test at 90 days. FIG. 29B shows that in the oral glucose tolerance test these mice also showed 23% reduction in blood glucose compared at the peak oral glucose tolerance test of 30 minutes compared with the control high fat diet group. FIG. 29C shows that mice treated with compound 8 showed a significant (P<0.02) decrease by 26% in fasting blood glucose compared with the control high fat diet group.

FIG. 30 shows that rats treated with compound 8 showed 4% decrease in systolic blood pressure and 8% decrease in diastolic blood pressure, then the vehicle group.

FIG. 31 shows that hamsters treated with compound 8 showed a significant decrease (P<0.05) by 31% in triglycerides compared with the high fructose fed group.

FIG. 32 shows that mice administered with compound 8 showed a 59% decrease of TNF-α from the LPS group.

FIG. 33A shows that mice treated with compound 9 showed a significant (P<0.0001) decrease by 5% in body weight when compared to the high fat diet control group. FIG. 33B shows mice treated with compound 9 showed a significant (P<0.0001) decrease by 15% in percent body weight when compared to the high fat diet control group.

FIG. 34A shows the effect of compound 9 on oral glucose tolerance test at Day 90. FIG. 34B shows that mice treated with compound 9 showed 8% reduction in blood glucose compared at the peak oral glucose tolerance test of 30 minutes compared with the control high fat diet group.

DETAILED DESCRIPTION OF THE INVENTION

In an embodiment of the present invention, the groups represented as R₁, R₂, R₃, R₄ and R₅ on ring A are predominantly hydrogen.

In an embodiment of the present invention, the group represented by R₇ is a carbonyl group through which free amino group containing molecules can form condensates. R₇ can also be selected from groups such as ethanedithiol and propanedithiol.

In an embodiment of the present invention, the styryl ring represented as ring A can contain one or multiple side chain substituents ranging from hydrogen, phenoxy, amino, sulphonyl, substituted, unsubstituted, straight chain or branched alkyls derivatives, halogens, and the like. This also defines the range of substituents accommodated by R₁, R₂, R₃, R₄ and R₅.

In an embodiment of the present invention, the groups represented by R₆ and R₈ on ring B can be selected from hydrogen, Hydroxy, alkoxy and branched or unbranched alkyl derivatives.

In an embodiment of the present invention, the groups represented by X and Y on ring B can be selected from hydrogen or Halogens like fluorine, chlorine, bromine, and iodine.

Pharmaceutically acceptable salts forming part of this invention include base addition salts such as alkali metal salts like Li, Na, and K salts, alkaline earth metal salts like Ca and Mg salts, salts of organic bases such as lysine, arginine, guanidine, diethanolamine, chlorine and the like, ammonium or substituted ammonium salts. Salts may include acid addition salts which are sulphates, nitrates, phosphates, perchlorates, borates, hydrohalides, acetates, tartarates, maleates, citrates, succinates, palmoates, methanesulphonates, benzoates, ascorbates, glycerophosphates, ketoglutarates and the like. Pharmaceutically acceptable solvates may be hydrates or comprising other solvents of crystallization such as alcohols

More preferably, the present innovation relates to novel Styryl Carboxylate compounds of formula (I),

their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates, novel intermediates and pharmaceutical compositions containing them, wherein, the groups represented as R₆ and R₈, in the ring B are selected from hydrogen and alkoxy derivatives. The group represented by R₇ on ring B will be a carbonyl group which forms Schiff bases with compounds having a free amino group and forms thioketalization with compounds like ethanedithiol and propandithiol. The benzene ring represented as Ring A can contain substituents represented by R₁, R₂, R₃, R₄ and R₅ that are selected from linear or branched, substituted or unsubstituted (C₁ to C₁₂) alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, hexyl, octyl, nonyl and the like; substituted or unsubstituted (C₁-C₁₂) alkoxy group such as methoxy, ethoxy, propoxy, butoxy and the like; hydroxyl group or extended chain through an alkyloxy ester or un-substituted or substituted aryloxy ester groups; amines, sulphonyl, halogens and the like. The groups represented by X and Y on ring B are preferentially selected from hydrogen and Halogens like fluorine, chlorine, bromine and iodine.

The formula of the useful compounds synthesized in this present are listed below.

-   3-Phenyl-acrylic acid 4-(hydroxyimino-methyl)-phenyl ester (C1) -   4-((E)-ureidomethyl)phenyl cinnamate (C2) -   4-(1,3-dithian-2-yl)phenyl cinnamate (C3) -   3-Phenyl-acrylic acid     4-benzylidineamino-3′-hydroxyaniline-2-methoxy-phenyl ester (C4) -   4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl cinnamate (C5) -   (E)-ethyl     4-(4-(cinnamoyloxy)-3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate     (C6) -   (E)-ethyl     4-(4-(cinnamoyloxy)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate     (C7) -   3-Phenyl-acrylic acid 4-(hydroxyimino-methyl)-2-methoxy-phenyl ester     (C8) -   2-methoxy-4-((E)-ureidomethyl)phenyl cinnamate (C9) -   4-[3-Methoxy-4-(3-phenyl-acryloyloxy)-phenyl]-6-Methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic     acid ethyl ester (C10) -   3-phenyl-acrylicacid4-[(2,4-dinitro-phenyl)-hydrazonomethyl]-phenyl     ester (C11) -   4-formyl-2-methoxyphenyl cinnamate -   2-chloro-4-formyl-6-methoxyphenyl cinnamate -   2-bromo-4-formyl-6-methoxyphenyl cinnamate -   4-formylphenyl cinnamate -   (E)-4-formyl-2-methoxyphenyl 3-(3-chlorophenyl)acrylate -   (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(3-chlorophenyl)acrylate -   (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(3-chlorophenyl)acrylate -   (E)-4-formylphenyl 3-(3-chlorophenyl)acrylate -   (E)-4-formyl-2-methoxyphenyl 3-(3-bromophenyl)acrylate -   (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(3-bromophenyl)acrylate -   (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(3-bromophenyl)acrylate -   (E)-4-formylphenyl 3-(3-bromophenyl)acrylate -   (E)-4-formyl-2-methoxyphenyl 3-(3-methoxyphenyl)acrylate -   (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate -   (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate -   (E)-4-formylphenyl 3-(3-methoxyphenyl)acrylate -   (E)-4-formyl-2-methoxyphenyl 3-(4-chlorophenyl)acrylate -   (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(4-chlorophenyl)acrylate -   (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(4-chlorophenyl)acrylate -   (E)-4-formylphenyl 3-(4-chlorophenyl)acrylate -   (E)-4-formyl-2-methoxyphenyl 3-(4-bromophenyl)acrylate -   (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(4-bromophenyl)acrylate -   (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(4-bromophenyl)acrylate -   (E)-4-formylphenyl 3-(4-bromophenyl)acrylate -   (E)-4-formyl-2-methoxyphenyl 3-(4-methoxyphenyl)acrylate -   (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate -   (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate -   (E)-4-formylphenyl 3-(4-methoxyphenyl)acrylate -   4-((E)-((E)-4-(cinnamoyloxy)-3-methoxybenzylidene)amino)benzoic acid -   4-((E)-((E)-3-chloro-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)benzoic     acid -   4-((E)-((E)-3-bromo-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)benzoic     acid -   4-((E)-((E)-4-(cinnamoyloxy)benzylidene)amino)benzoic acid -   4-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)benzoic     acid -   4-((E)-((E)-3-chloro-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic     acid -   4-((E)-((E)-3-bromo-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic     acid -   4-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)benzylidene)amino)benzoic     acid -   4-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)benzoic     acid -   4-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)benzoic     acid -   4-((E)-((E)-3-bromo-4-((E)-3-(3-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic     acid -   4-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)benzylidene)amino)benzoic     acid -   4-((E)-((E)-3-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic     acid -   4-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic     acid -   4-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic     acid -   4-((E)-((E)-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic     acid -   4-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)benzoic     acid -   4-((E)-((E)-3-chloro-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic     acid -   4-((E)-((E)-3-bromo-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic     acid -   4-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)benzylidene)amino)benzoic     acid -   4-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)benzoic     acid -   4-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)benzoic     acid -   4-((E)-((E)-3-bromo-4-((E)-3-(4-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic     acid -   4-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)benzylidene)amino)benzoic     acid -   4-((E)-((E)-3-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic     acid -   4-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic     acid -   4-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic     acid -   4-((E)-((E)-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic     acid -   2-((E)-((E)-4-(cinnamoyloxy)-3-methoxybenzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-3-chloro-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-3-bromo-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-4-(cinnamoyloxy)benzylidene)amino)-3-methylbutanoic acid -   2-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-3-chloro-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-3-bromo-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-3-bromo-4-((E)-3-(3-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-3-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-3-chloro-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-3-bromo-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-3-bromo-4-((E)-3-(4-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-3-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic     acid -   2-((E)-((E)-4-(cinnamoyloxy)-3-methoxybenzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-3-chloro-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-3-bromo-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-4-(cinnamoyloxy)benzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-3-chloro-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-3-bromo-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-3-bromo-4-((E)-3-(3-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-3-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-3-chloro-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-3-bromo-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-3-bromo-4-((E)-3-(4-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-3-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic     acid -   2-((E)-((E)-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic     acid -   4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl cinnamate -   2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl cinnamate -   2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl cinnamate -   4-((E)-(hydroxyimino)methyl)phenyl cinnamate -   (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl     3-(3-chlorophenyl)acrylate -   (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl     3-(3-chlorophenyl)acrylate -   (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl     3-(3-chlorophenyl)acrylate -   (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(3-chlorophenyl)acrylate -   (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl     3-(3-bromophenyl)acrylate -   (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl     3-(3-bromophenyl)acrylate -   (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl     3-(3-bromophenyl)acrylate -   (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(3-bromophenyl)acrylate -   (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl     3-(3-methoxyphenyl)acrylate -   (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl     3-(3-methoxyphenyl)acrylate -   (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl     3-(3-methoxyphenyl)acrylate -   (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(3-methoxyphenyl)acrylate -   (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl     3-(4-chlorophenyl)acrylate -   (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl     3-(4-chlorophenyl)acrylate -   (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl     3-(4-chlorophenyl)acrylate -   (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(4-chlorophenyl)acrylate -   (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl     3-(4-bromophenyl)acrylate -   (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl     3-(4-bromophenyl)acrylate -   (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl     3-(4-bromophenyl)acrylate -   (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(4-bromophenyl)acrylate -   (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl     3-(4-methoxyphenyl)acrylate -   (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl     3-(4-methoxyphenyl)acrylate -   (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl     3-(4-methoxyphenyl)acrylate -   (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(4-methoxyphenyl)acrylate -   2-methoxy-4-((E)-ureidomethyl)phenyl cinnamate -   2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl cinnamate -   2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl cinnamate -   4-((E)-ureidomethyl)phenyl cinnamate -   (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-chlorophenyl)acrylate -   (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl     3-(3-chlorophenyl)acrylate -   (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl     3-(3-chlorophenyl)acrylate -   (E)-4-((E)-ureidomethyl)phenyl 3-(3-chlorophenyl)acrylate -   (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-bromophenyl)acrylate -   (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl     3-(3-bromophenyl)acrylate -   (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl     3-(3-bromophenyl)acrylate -   (E)-4-((E)-ureidomethyl)phenyl 3-(3-bromophenyl)acrylate -   (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-methoxyphenyl)acrylate -   (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl     3-(3-methoxyphenyl)acrylate -   (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl     3-(3-methoxyphenyl)acrylate -   (E)-4-((E)-ureidomethyl)phenyl 3-(3-methoxyphenyl)acrylate -   (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-chlorophenyl)acrylate -   (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl     3-(4-chlorophenyl)acrylate -   (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl     3-(4-chlorophenyl)acrylate -   (E)-4-((E)-ureidomethyl)phenyl 3-(4-chlorophenyl)acrylate -   (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-bromophenyl)acrylate -   (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl     3-(4-bromophenyl)acrylate -   (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl     3-(4-bromophenyl)acrylate -   (E)-4-((E)-ureidomethyl)phenyl 3-(4-bromophenyl)acrylate -   (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-methoxyphenyl)acrylate -   (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl     3-(4-methoxyphenyl)acrylate -   (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl     3-(4-methoxyphenyl)acrylate -   (E)-4-((E)-ureidomethyl)phenyl 3-(4-methoxyphenyl)acrylate -   4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl cinnamate -   2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl     cinnamate -   2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl     cinnamate -   4-((E)-(4-hydroxyphenylimino)methyl)phenyl cinnamate -   (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl     3-(3-chlorophenyl)acrylate -   (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl     3-(3-chlorophenyl)acrylate -   (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl     3-(3-chlorophenyl)acrylate -   (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl     3-(3-chlorophenyl)acrylate -   (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl     3-(3-bromophenyl)acrylate -   (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl     3-(3-bromophenyl)acrylate -   (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl     3-(3-bromophenyl)acrylate -   (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl     3-(3-bromophenyl)acrylate -   (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl     3-(3-methoxyphenyl)acrylate -   (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl     3-(3-methoxyphenyl)acrylate -   (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl     3-(3-methoxyphenyl)acrylate -   (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl     3-(3-methoxyphenyl)acrylate -   (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl     3-(4-chlorophenyl)acrylate -   (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl     3-(4-chlorophenyl)acrylate -   (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl     3-(4-chlorophenyl)acrylate -   (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl     3-(4-chlorophenyl)acrylate -   (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl     3-(4-bromophenyl)acrylate -   (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl     3-(4-bromophenyl)acrylate -   (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl     3-(4-bromophenyl)acrylate -   (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl     3-(4-bromophenyl)acrylate -   (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl     3-(4-methoxyphenyl)acrylate -   (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl     3-(4-methoxyphenyl)acrylate -   (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl     3-(4-methoxyphenyl)acrylate -   (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl     3-(4-methoxyphenyl)acrylate -   4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-2-methoxyphenyl cinnamate -   2-chloro-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl     cinnamate -   2-bromo-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl     cinnamate -   4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)phenyl cinnamate -   (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-2-methoxyphenyl     3-(3-chlorophenyl)acrylate -   (E)-2-chloro-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl     3-(3-chlorophenyl)acrylate -   (E)-2-bromo-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl     3-(3-chlorophenyl)acrylate -   (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)phenyl     3-(3-chlorophenyl)acrylate -   (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-2-methoxyphenyl     3-(3-bromophenyl)acrylate -   (E)-2-chloro-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl     3-(3-bromophenyl)acrylate -   (E)-2-bromo-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl     3-(3-bromophenyl)acrylate -   (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)phenyl     3-(3-bromophenyl)acrylate -   (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-2-methoxyphenyl     3-(3-methoxyphenyl)acrylate -   (E)-2-chloro-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl     3-(3-methoxyphenyl)acrylate -   (E)-2-bromo-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl     3-(3-methoxyphenyl)acrylate -   (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)phenyl     3-(3-methoxyphenyl)acrylate -   (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-2-methoxyphenyl     3-(4-chlorophenyl)acrylate -   (E)-2-chloro-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl     3-(4-chlorophenyl)acrylate -   (E)-2-bromo-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl     3-(4-chlorophenyl)acrylate -   (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)phenyl     3-(4-chlorophenyl)acrylate -   (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-2-methoxyphenyl     3-(4-bromophenyl)acrylate -   (E)-2-chloro-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl     3-(4-bromophenyl)acrylate -   (E)-2-bromo-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl     3-(4-bromophenyl)acrylate -   (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)phenyl     3-(4-bromophenyl)acrylate -   (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-2-methoxyphenyl     3-(4-methoxyphenyl)acrylate -   (E)-2-chloro-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl     3-(4-methoxyphenyl)acrylate -   (E)-2-bromo-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl     3-(4-methoxyphenyl)acrylate -   (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)phenyl     3-(4-methoxyphenyl)acrylate

The list also consists of the IUPAC names of the compounds given the table below—

S.No R7 R8 R6 R2 R3  1. O OCH₃ H H H  2. O OCH₃ Cl H H  3. O OCH₃ Br H H  4. O H H H H  5. O OCH₃ H Cl H  6. O OCH₃ Cl Cl H  7. O OCH₃ Br Cl H  8. O H H Cl H  9. O OCH₃ H Br H  10. O OCH₃ Cl Br H  11. O OCH₃ Br Br H  12. O H H Br H  13. O OCH₃ H OCH₃ H  14. O OCH₃ Cl OCH₃ H  15. O OCH₃ Br OCH₃ H  16. O H H OCH₃ H  17. O OCH₃ H H Cl  18. O OCH₃ Cl H Cl  19. O OCH₃ Br H Cl  20. O H H H Cl  21. O OCH₃ H H Br  22. O OCH₃ Cl H Br  23. O OCH₃ Br H Br  24. O H H H Br  25. O OCH₃ H H OCH₃  26. O OCH₃ Cl H OCH₃  27. O OCH₃ Br H OCH₃  28. O H H H OCH₃  29.

OCH₃ H H H  30.

OCH₃ Cl H H  31.

OCH₃ Br H H  32.

H H H H  33.

OCH₃ H Cl H  34.

OCH₃ Cl Cl H  35.

OCH₃ Br Cl H  36.

H H Cl H  37.

OCH₃ H Br H  38.

OCH₃ Cl Br H  39.

OCH₃ Br Br H  40.

H H Br H  41.

OCH₃ H OCH₃ H  42.

OCH₃ Cl OCH₃ H  43.

OCH₃ Br OCH₃ H  44.

H H OCH₃ H  45.

OCH₃ H H Cl  46.

OCH₃ Cl H Cl  47.

OCH₃ Br H Cl  48.

H H H Cl  49.

OCH₃ H H Br  50.

OCH₃ Cl H Br  51.

OCH₃ Br H Br  52.

H H H Br  53.

OCH₃ H H OCH₃  54.

OCH₃ Cl H OCH₃  55.

OCH₃ Br H OCH₃  56.

H H H OCH₃  57.

OCH₃ H H H  58.

OCH₃ Cl H H  59.

OCH₃ Br H H  60.

H H H H  61.

OCH₃ H Cl H  62.

OCH₃ Cl Cl H  63.

OCH₃ Br Cl H  64.

H H Cl H  65.

OCH₃ H Br H  66.

OCH₃ Cl Br H  67.

OCH₃ Br Br H  68.

H H Br H  69.

OCH₃ H OCH₃ H  70.

OCH₃ Cl OCH₃ H  71.

OCH₃ Br OCH₃ H  72.

H H OCH₃ H  73.

OCH₃ H H Cl  74.

OCH₃ Cl H Cl  75.

OCH₃ Br H Cl  76.

H H H Cl  77.

OCH₃ H H Br  78.

OCH₃ Cl H Br  79.

OCH₃ Br H Br  80.

H H H Br  81.

OCH₃ H H OCH₃  82.

OCH₃ Cl H OCH₃  83.

OCH₃ Br H OCH₃  84.

H H H OCH₃  85.

OCH₃ H H H  86.

OCH₃ Cl H H  87.

OCH₃ Br H H  88.

H H H H  89.

OCH₃ H Cl H  90.

OCH₃ Cl Cl H  91.

OCH₃ Br Cl H  92.

H H Cl H  93.

OCH₃ H Br H  94.

OCH₃ Cl Br H  95.

OCH₃ Br Br H  96.

H H Br H  97.

OCH₃ H OCH₃ H  98.

OCH₃ Cl OCH₃ H  99.

OCH₃ Br OCH₃ H 100.

H H OCH₃ H 101.

OCH₃ H H Cl 102.

OCH₃ Cl H Cl 103.

OCH₃ Br H Cl 104.

H H H Cl 105.

OCH₃ H H Br 106.

OCH₃ Cl H Br 107.

OCH₃ Br H Br 108.

H H H Br 109.

OCH₃ H H OCH₃ 110.

OCH₃ Cl H OCH₃ 111.

OCH₃ Br H OCH₃ 112.

H H H OCH₃ 113. NOH OCH₃ H H H 114. NOH OCH₃ Cl H H 115. NOH OCH₃ Br H H 116. NOH H H H H 117. NOH OCH₃ H Cl H 118. NOH OCH₃ Cl Cl H 119. NOH OCH₃ Br Cl H 120. NOH H H Cl H 121. NOH OCH₃ H Br H 122. NOH OCH₃ Cl Br H 123. NOH OCH₃ Br Br H 124. NOH H H Br H 125. NOH OCH₃ H OCH₃ H 126. NOH OCH₃ Cl OCH₃ H 127. NOH OCH₃ Br OCH₃ H 128. NOH H H OCH₃ H 129. NOH OCH₃ H H Cl 130. NOH OCH₃ Cl H Cl 131. NOH OCH₃ Br H Cl 132. NOH H H H Cl 133. NOH OCH₃ H H Br 134. NOH OCH₃ Cl H Br 135. NOH OCH₃ Br H Br 136. NOH H H H Br 137. NOH OCH₃ H H OCH₃ 138. NOH OCH₃ Cl H OCH₃ 139. NOH OCH₃ Br H OCH₃ 140. NOH H H H OCH₃ 141. NCONH₂ OCH₃ H H H 142. NCONH₂ OCH₃ Cl H H 143. NCONH₂ OCH₃ Br H H 144. NCONH₂ H H H H 145. NCONH₂ OCH₃ H Cl H 146. NCONH₂ OCH₃ Cl Cl H 147. NCONH₂ OCH₃ Br Cl H 148. NCONH₂ H H Cl H 149. NCONH₂ OCH₃ H Br H 150. NCONH₂ OCH₃ Cl Br H 151. NCONH₂ OCH₃ Br Br H 152. NCONH₂ H H Br H 153. NCONH₂ OCH₃ H OCH₃ H 154. NCONH₂ OCH₃ Cl OCH₃ H 155. NCONH₂ OCH₃ Br OCH₃ H 156. NCONH₂ H H OCH₃ H 157. NCONH₂ OCH₃ H H Cl 158. NCONH₂ OCH₃ Cl H Cl 159. NCONH₂ OCH₃ Br H Cl 160. NCONH₂ H H H Cl 161. NCONH₂ OCH₃ H H Br 162. NCONH₂ OCH₃ Cl H Br 163. NCONH₂ OCH₃ Br H Br 164. NCONH₂ H H H Br 165. NCONH₂ OCH₃ H H OCH₃ 166. NCONH₂ OCH₃ Cl H OCH₃ 167. NCONH₂ OCH₃ Br H OCH₃ 168. NCONH₂ H H H OCH₃ 169.

OCH₃ H H H 170.

OCH₃ Cl H H 171.

OCH₃ Br H H 172.

H H H H 173.

OCH₃ H Cl H 174.

OCH₃ Cl Cl H 175.

OCH₃ Br Cl H 176.

H H Cl H 177.

OCH₃ H Br H 178.

OCH₃ Cl Br H 179.

OCH₃ Br Br H 180.

H H Br H 181.

OCH₃ H OCH₃ H 182.

OCH₃ Cl OCH₃ H 183.

OCH₃ Br OCH₃ H 184.

H H OCH₃ H 185.

OCH₃ H H Cl 186.

OCH₃ Cl H Cl 187.

OCH₃ Br H Cl 188.

H H H Cl 189.

OCH₃ H H Br 190.

OCH₃ Cl H Br 191.

OCH₃ Br H Br 192.

H H H Br 193.

OCH₃ H H OCH₃ 194.

OCH₃ Cl H OCH₃ 195.

OCH₃ Br H OCH₃ 196.

H H H OCH₃ 197.

OCH₃ H H H 198.

OCH₃ Cl H H 199.

OCH₃ Br H H 200.

H H H H 201.

OCH₃ H Cl H 202.

OCH₃ Cl Cl H 203.

OCH₃ Br Cl H 204.

H H Cl H 205.

OCH₃ H Br H 206.

OCH₃ Cl Br H 207.

OCH₃ Br Br H 208.

H H Br H 209.

OCH₃ H OCH₃ H 210.

OCH₃ Cl OCH₃ H 211.

OCH₃ Br OCH₃ H 212.

H H OCH₃ H 213.

OCH₃ H H Cl 214.

OCH₃ Cl H Cl 215.

OCH₃ Br H Cl 216.

H H H Cl 217.

OCH₃ H H Br 218.

OCH₃ Cl H Br 219.

OCH₃ Br H Br 220.

H H H Br 221.

OCH₃ H H OCH₃ 222.

OCH₃ Cl H OCH₃ 223.

OCH₃ Br H OCH₃ 224.

H H H OCH₃

Preferred salts for the compounds listed above are hydrochloride, hydrobromide, sodium, potassium or magnesium.

According to another feature of this present invention, there is provided a process for the preparation of the compound represented by the formula I, wherein all symbols are as defined as earlier, as shown in scheme (I):

-   -   Structure (4a) is the equivalent structure of (4) where R₇ is as         described earlier. In cases where R₇=O, the reaction is only         until the second step.

The reaction of compound of general formula (1a) with thionyl chloride, where the groups R1, R2, R3, R4 and R5 of the compound (1a) have been defined earlier, to produce a compound of the general formula (1b) may be carried out in an inert atmosphere which may be maintained by using inert gases such as Nitrogen, Argon or Helium. Thionyl chloride is added drop wise to the compound (1a) which may be taken as such without any solvents. After addition of thionyl chloride, the reaction mixture is subjected to reflux. The reaction temperature may vary between 20° C. to 150° C., but more preferably between 60° C. to 90° C. The duration of the reaction may range from 1 to 24 hours, preferably between 4 to 6 hours. After refluxing the excess thionyl chloride is distilled off to obtain (1b).

The reaction of compound of general formula (1b) with a compound of general formula (2a) where the groups R6, R7, X and Y have been defined earlier may be carried out using a polar protic solvent like chloroform and in the presence of weak bases like DEA, TEA, Isopropylamine, pyridine, pipridine and the like, but more preferably with a base like TEA. The reaction temperature may range between 0 to 20° C., more preferably in the range of 5-10° C. The reaction time may range from 1 to 10 hours and following completion of the reaction, the product may be extracted from the reaction mixture by washing the organic phase with an aqueous solvent followed by precipitation using non polar solvents like butane, pentante, hexane, cyclohexane etc. to obtain compound of formula (3a).

The reaction of compound of general formula (3a) with an aliphatic or aromatic amines or amino acids, wherein the amino group reacts, is possible only when R7 is a keto functional group like (—CHO) or (C═O). This reaction may take place in the presence of any alcohol along with catalytic amounts of mineral acids such as sulphuric acid. The reaction temperature may vary from 0 to 100° C. preferably in the range of 50-70° C. and the reaction time may vary between 1 to 24 hours, preferably in the range of 4-7 hours. The schiff base or the imine thus formed may be precipitated or could be extracted after suitable workup procedures such as water quenching. The resultant molecule is the styryl carboxylate of general formula (4a) where the groups have been defined earlier.

The invention is explained in detail in the examples given below which are provided by way of illustration only and therefore should not be construed to limit the scope of the invention.

Example 1 Synthesis of 3-Phenyl-acrylic Acid 4-(hydroxyimino-methyl)-phenyl Ester (C1)

Step (i) Synthesis of Cinnamoyl Chloride

Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80° C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle stored. (Yield 53.0 g)

Step (ii) Synthesis of 3-Phenyl-acrylic Acid 4-formyl-phenyl Ester

4 hydroxy benzaldehyde (14.69 g) was taken in a clean and dry two neck round bottom flask and chloroform (200 ml) was added with constant stirring. The reaction mixture was cooled to 10-15 and Nicotonyl chloride (20.0 g) was added drop wise. Stirring was continued for another 15 minutes and TEA (16.44 ml) was added drop wise and the reaction was allowed to stir for 4 hours. It was then transferred to a separating funnel and washed twice with water (2×250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2×250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vaccum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 15.7 g)

Step (iii) Synthesis of 3-Phenyl-acrylic Acid 4-(hydroxyimino-methyl)-phenyl Ester

Stage (ii) compound (2.5 g) was taken in a clean and dry round bottom flask and Methanol (25 ml) was added. The reaction mixture was cooled to 15 C and sodium acetate (2.5 g) was added. Hydroxylamine hydrochloride (1.25 g) dissolved in 10 ml of water was added drop wise to the reaction mixture with constant stirring. Stirring was continued for 4 hours at room temperature. The reaction mixture was then transferred to a beaker containing 100 ml of water. The precipitated solid was filtered, washed with water and then followed by hexane and dried. (Yield 1.2 g)

The synthesized compound was confirmed by proton NMR.

7.25 (d, 1H), 7.61 (d, 1H), 6.67 (d, 1H), 6.64 (d, 1H), 8.17 (s, 1H), 1.28 (s, 1H), 6.674 (d, J=16.5, 1H), 7.929 (d, J=16.5, 1H), 7.28 (d, 1H), 7.24 (t, 1H), 7.23 (t, 1H), 7.46 (t, 1H), 7.45 (d, 1H)

Example 2 Synthesis of 3-Phenyl-acrylic Acid 4-(hydroxyimino-methyl)-2-methoxy-phenyl Ester (C8)

Step (i) Synthesis of Cinnamoyl Chloride

Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80° C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle stored. (Yield 53.0 g)

Step (ii) Synthesis of 3-Phenyl-acrylic Acid 4-formyl-2-methoxy-phenyl Ester (Cinnamoyl Vanillin)

Vanillin (22.8 g) was taken in a clean and dry round bottom flask and chloroform (200 ml) was added whilst stirring. The reaction mixture was cooled to 5-10° C. Cinnamoyl chloride (25.0 g) was added drop wise. Stirring was continued for another 15 minutes and TEA (20.55 ml) was added drop wise while stirring. The reaction was allowed to continue for 5 hours with constant stirring. The reaction mixture was then transferred to a 1 L beaker and washed twice with water (2×250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2×250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vacuum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 16.2 g)

Step (iii) Synthesis of 3-Phenyl-acrylic Acid 4-(hydroxyimino-methyl)-2-methoxy-phenyl Ester

Cinnamoyl vanniline (5.7 g) was taken in a round bottom flask and methanol (50 ml) was added. The reaction mixture was cooled to 15° C. and sodium acetate (7.89 g) was added. Hydroxyl amine (2.8 g) was dissolved in (25 ml) of water and this was added drop wise to the reaction mixture under constant stirring. The reaction mixture was allowed to stir for 4 hours and then transferred into a beaker containing 100 ml of water. The precipitated solid was filtered, washed with water, followed by hexane and then dried. (Yield 2.8 g)

7.25 (d, 1H), 7.61 (d, 1H), 6.67 (d, 1H), 3.85 (s, 3H), 8.17 (s, 1H), 1.28 (s, 1H), 6.674 (d, J=16.5, 1H), 7.929 (d, J=16.5, 1H), 7.28 (d, 1H), 7.24 (t, 1H), 7.23 (t, 1H), 7.46 (t, 1H), 7.45 (d, 1H)

Example 3 Synthesis of 4-[3-Methoxy-4-(3-phenyl-acryloyloxy)-phenyl]-6-Methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic Acid Ethyl Ester (C10)

Step (i) Synthesis of Cinnamoyl Chloride

Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80° C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle and stored. (Yield 53.0 g)

Step (ii) Synthesis of 3-Phenyl-acrylic Acid 4-formyl-2-methoxy-phenyl Ester (Cinnamoyl Vanillin)

Vanillin (22.8 g) was taken in a clean and dry round bottom flask and chloroform (200 ml) was added whilst stirring. The reaction mixture was cooled to 5-10° C. Cinnamoyl chloride (25.0 g) was added drop wise. Stirring was continued for another 15 minutes and TEA (20.55 ml) was added drop wise while stirring. The reaction was allowed to continue for 5 hours with constant stirring. The reaction mixture was then transferred to a 1 L beaker and washed twice with water (2×250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2×250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vacuum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 16.2 g)

Step (iii) Synthesis of 4-[3-Methoxy-4-(3-phenyl-acryloyloxy)-phenyl]-6-Methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic Acid Ethyl Ester

Cinnamoyl vanilline (3.0 g), Urea (0.64 g) and Ethylacetoacetate (2.56 ml) were taken in a clean and dry three neck round bottom flask and Methanol (50 ml) and Sulphuric acid (5 drops) were added. This reaction mixture was subjected to reflux at 60-80° C. for 5 hours. After reflux, the reaction mixture was transferred to a beaker containing 200 ml of water. The precipitated solid was filtered, washed with water and followed with hexane and then dried. (Yield 1.42 g)

5.61 (s, 1H), 5.53 (s, 1H), 6.51 (s, 1H), 6.83 (d, 2H), 4.21 (m, 2H), 1.26 (t, 3H), 2.23 (s, 3H), 3.91 (s, 3H), 6.8 (d, 1H, J=16.5), 7.9 (d, 1H, J=16.5), 7.40 (d, 2H), 7.25 (t, 1H)

Example 4 Synthesis of 2-methoxy-4-((E)-ureidomethyl)phenyl Cinnamate (C9)

Synthesis of Cinnamoyl Chloride Step (i)

Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80° C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle stored. (Yield 53.0 g)

Step (ii) Synthesis of 3-Phenyl-acrylic Acid 4-formyl-2-methoxy-phenyl Ester (Cinnamoyl Vanillin)

Vanillin (22.8 g) was taken in a clean and dry round bottom flask and chloroform (200 ml) was added whilst stirring. The reaction mixture was cooled to 5-10° C. Cinnamoyl chloride (25.0 g) was added drop wise. Stirring was continued for another 15 minutes and TEA (20.55 ml) was added drop wise while stirring. The reaction was allowed to continue for 5 hours with constant stirring. The reaction mixture was then transferred to a 1 L beaker and washed twice with water (2×250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2×250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vacuum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 16.2 g)

Step (iii) Synthesis of 2-methoxy-4-((E)-ureidomethyl)phenyl Cinnamate

Cinnamoyl vanillin (5.0 g) was taken in a two next round bottom flask along with urea (2.2 g). Toulene (25 ml) was added and stirred and catalytic amounts of Paratoulylsulphonic acid (0.1 g) was added. The reaction mixture was refluxed for 4 hours at 100-110° C. After reflux the solvent was removed by distillation and the product was washed with water and followed by hexane and then dried. (Yield 3.12 g)

NMR Assignment

7.10 (1H, d), 7.20 (1H, d), 7.10 (1H, s), 3.80 (3H, s), 8.15 (1H, s), 6.20 (1H, d, J=16.5 MHz), 7.71 (1H, d, J=16.5 MHz), 7.35 (1H, d, Aromatic)

Example 5

Synthesis of 3-Phenyl-acrylic Acid 4-benzylidineamino-3′-hydroxyaniline-2-methoxy-Phenyl Ester (C4) Step (i) Synthesis of Cinnamoyl Chloride

Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80° C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle stored. (Yield 53.0 g)

Step (ii) Synthesis of 3-Phenyl-acrylic Acid 4-formyl-2-methoxy-phenyl Ester (Cinnamoyl Vanillin)

Vanillin (22.8 g) was taken in a clean and dry round bottom flask and chloroform (200 ml) was added whilst stirring. The reaction mixture was cooled to 5-10° C. Cinnamoyl chloride (25.0 g) was added drop wise. Stirring was continued for another 15 minutes and TEA (20.55 ml) was added drop wise while stirring. The reaction was allowed to continue for 5 hours with constant stirring. The reaction mixture was then transferred to a 1 L beaker and washed twice with water (2×250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2×250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vacuum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 16.2 g)

Cinnamoyl vanillin (1.5 g) was taken in a clean two neck round bottom flask and Ethanol (25 ml) was added with stirring. 3-Aminophenol (0.6 g) was added lot by lot with constant stirring. After completion of addition, 2 drops of sulphuric acid was added. The reaction mixture was refluxed for 4 hours at 75-80° C. The solid product formed was filtered and washed with Ethanol and followed by water and finally by hexane and dried. (Yield 0.89 g)

NMR Assignment

6.81 (1H, d), 7.15 (1H, d), 7.10 (1H, s), 3.91 (3H, s), 6.72 to 7.10 (Aromatic), 6.20 (1H, d, J=16.5 MHz), 7.71 (1H, d, J=16.5 MHz), 7.15 to 7.35 (Aromatic)

Example 6

Synthesis of 3-phenyl-acrylicacid4-[(2,4-dinitro-phenyl)-hydrazonomethyl]-phenyl Ester (C11) Step (i) Synthesis of Cinnamoyl Chloride

Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80° C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle stored. (Yield 53.0 g)

Step (ii) Synthesis of 3-Phenyl-acrylic Acid 4-formyl-phenyl Ester

4-hydroxy benzaldehyde (14.69 g) was taken is a clean and dry two neck round bottom flask and Chloroform (200 ml) was added whilst stirring. The reaction mixture was cooled to 5-10° C. Nicotinyl chloride (20.0 g) was added drop wise and stirring was continued for 15 minutes. TEA (16.44 ml) was added drop wise and the reaction was allowed to stir for 4 hours. It was then transferred to a separating funnel and washed twice with water (2×250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2×250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vaccum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 15.7 g)

Step (iii) Synthesis of 3-phenyl-acrylicacid4-[(2,4-dinitro-phenyl)-hydrazonomethyl]-phenyl Ester

Cinnamoyl 4-hydroxy benzaldehyde (1 g) was taken in a clean and dry round bottom flask and methanol (10 ml) was added. 2,4 Dinitrophenylhydrazine (0.00 g) was added slowly into the reaction mixture and methanol (20 ml) was added. The reaction mixture was allowed to stir for 3 hours at room temperature. The solid formed was then filtered and washed with water and followed by hexane. (Yield 0.85 g)

NMR Assignment

6.81 (1H, d), 7.15 (1H, d), 7.6 (1H, s), 7.12 (1H, d), 8.30 (1H, s), 5.0 (1H, s), 8.5 (1H, s), 8.21 (1H, d), 6.62 (1H, d), 6.20 (1H, d, J=16.5 MHz), 7.71 (1H, d, J=16.5 MHz), 7.15 to 7.35 (Aromatic)

Example 7

Synthesis of 4-((E)-ureidomethyl)phenyl Cinnamate (C2) Step (i) Synthesis of Cinnamoyl Chloride

Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80° C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle stored. (Yield 53.0 g)

Step (ii) Synthesis of 3-Phenyl-acrylic Acid 4-formyl-phenyl Ester

4 hydroxy benzaldehyde (14.69 g) was taken in a clean and dry two neck round bottom flask and chloroform (200 ml) was added with constant stirring. The reaction mixture was cooled to 10-15 and Nicotonyl chloride (20.0 g) was added drop wise. Stirring was continued for another 15 minutes and TEA (16.44 ml) was added drop wise and the reaction was allowed to stir for 4 hours. It was then transferred to a separating funnel and washed twice with water (2×250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2×250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vaccum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 15.7 g)

Step (iii) Synthesis of 4-((E)-ureidomethyl)phenyl Cinnamate

Compound of step 2 (5 g) was taken in a clean and dry two neck round bottom flask and PTSA (3.8 g) was added. Urea (1.3 g) was then added and Toulene (50 ml) was added with stirring. The reaction mixture was refluxed for 5 hours at 100-110 and allowed to cool over night at room temperature. The precipitated compound was filtered, washed with water and followed by hexane and dried. (Yield 3.34 g)

NMR Assignment

7.10 to 7.60 (Aromatic), 8.20 (1H, s), 5.0 (2H, s), 6.20 (1H, d, J=16.5 MHz), 7.71 (1H, d, J=16.5 MHz), 7.15 to 7.35 (Aromatic)

Example 8

Synthesis of 4-(1,3-dithian-2-yl)phenyl Cinnamate (C3) Step (i) Synthesis of Cinnamoyl Chloride

Cinnamic acid (50.0 g) was taken in a clean and dry three neck round bottom flask and thionyl chloride (175 ml) was added drop wise with constant stirring. The reaction mixture was refluxed at 70-80° C. for five hours. After reflux the excess thionyl chloride was distilled off. Hexane was added and distillation was performed again to remove any traces of thionyl chloride. The product was then transferred to an amberlite bottle stored. (Yield 53.0 g)

Step (ii) Synthesis of 3-Phenyl-acrylic Acid 4-formyl-phenyl Ester

4 hydroxy benzaldehyde (14.69 g) was taken in a clean and dry two neck round bottom flask and chloroform (200 ml) was added with constant stirring. The reaction mixture was cooled to 10-15 and Nicotonyl chloride (20.0 g) was added drop wise. Stirring was continued for another 15 minutes and TEA (16.44 ml) was added drop wise and the reaction was allowed to stir for 4 hours. It was then transferred to a separating funnel and washed twice with water (2×250 ml). The chloroform layer was separated and further washed with 10% NaOH solution (2×250 ml) and then dried with anhydrous sodium sulphate. The chloroform layer was then filtered and concentrated under vaccum. Hexane was then added to the concentrated chloroform layer and the solid formed was filtered and dried. (Yield 15.7 g)

Step (iii) Synthesis of 4-(1,3-dithian-2-yl)phenyl Cinnamate

Compound from step (ii) (6.0 g) was taken in a clean and dry two neck round bottom flask and Chloroform (60 ml) was added with stirring. 1,3 Dithiane (2.7 g) and catalytic amount of iodine (0.1 g) was added and the reaction mixture was allowed to stir at room temperature for 5 hours. It was then quenched with cold water and the organic layer was separated which was further washed with water. The chloroform layer was then concentrated and the solid obtained was filtered, washed with hexane and then dried. (Yield 7.0 g)

NMR Assignment

2.44 (4H, t), 2.03 (2H, m), 4.5 (2H, s), 6.8-7.1 (Aromatic), 6.20 (1H, d, J=16.5 MHz), 7.71 (1H, d, J=16.5 MHz), 7.15-7.35 (Aromatic) 

1. A compound of Formula (I)

or a pharmaceutically acceptable salt thereof, wherein R₁, R₂, R₃, R₄ and R₅ is selected from a group consisting of hydrogen, phenoxy, amino, sulphonyl, substituted or unsubstituted straight chain or branched alkyls derivatives and halogens; wherein each of R₆ and R₈ on ring B is selected from the group consisting of hydrogen, hydroxy, alkoxy and branched or unbranched alkyl derivatives; wherein R₇ is selected from a group consisting of (i) a carbonyl group through which free amino group containing molecules can form condensates, (ii) an ethanedithiol group and (iii) a propanedithiol group; and wherein each of X and Y on ring B is a halogen.
 2. The compound of claim 1 wherein R₁, R₂, R₃, R₄ and R₅ are hydrogens.
 3. The compound of claim 1 comprising a pharmaceutically acceptable salt of Formula (I).
 4. The compound of claim 3 wherein the salt is selected from the group consisting of a base addition salt of Li, Na, K, Ca and Mg, salts of organic bases selected from the group consisting of lysine, arginine, guanidine, diethanolamine, and salts comprising chlorine, ammonium or substituted ammonium salts.
 5. The compound of claim 3 wherein the salt is selected from the group consisting of sulphates, nitrates, phosphates, perchlorates, borates, hydrohalides, acetates, tartarates, maleates, citrates, succinates, palmoates, methanesulphonates, benzoates, ascorbates, glycerophosphates and ketoglutarates.
 7. The compound of claim 1 wherein R₇ and R₈ are selected from the group consisting of hydrogen derivatives and alkoxy derivatives.
 8. The compound of claim 1 wherein R₇ is a carbonyl group which forms Schiff bases with compounds having a free amino group and performs a thioketalization reaction dithiol compounds.
 9. The compound of claim 1 wherein R₁, R₂, R₃, R₄ and R₅ is each selected from the group consisting of a linear or branched, substituted or unsubstituted (C₁ to C₁₂) alkyl group.
 10. The compound of claim 9 wherein said alkyl group is selected from the group consisting of a methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, hexyl, octyl and nonyl group, or a substituted or unsubstituted (C₁-C₁₂) alkoxy group such as methoxy, ethoxy, propoxy and butoxy group, or an alkyloxy ester or un-substituted or substituted aryloxy ester group, an amine, sulphonyl, halogen group and wherein X and Y are selected from a hydrogen or a halogen.
 11. The compound of claim 1 selected from the group consisting of: 3-Phenyl-acrylic acid 4-(hydroxyimino-methyl)-phenyl ester (C1) 4-((E)-ureidomethyl)phenyl cinnamate (C2) 4-(1,3-dithian-2-yl)phenyl cinnamate (C3) 3-Phenyl-acrylic acid 4-benzylidineamino-3′-hydroxyaniline-2-methoxy-phenyl ester (C4) 4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl cinnamate (C5) (E)-ethyl 4-(4-(cinnamoyloxy)-3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (C6) (E)-ethyl 4-(4-(cinnamoyloxy)phenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (C7) 3-Phenyl-acrylic acid 4-(hydroxyimino-methyl)-2-methoxy-phenyl ester (C8) 2-methoxy-4-((E)-ureidomethyl)phenyl cinnamate (C9) 4-[3-Methoxy-4-(3-phenyl-acryloyloxy)-phenyl]-6-Methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester (C10) 3-phenyl-acrylicacid4-[(2,4-dinitro-phenyl)-hydrazonomethyl]-phenyl ester (C11) 4-formyl-2-methoxyphenyl cinnamate 2-chloro-4-formyl-6-methoxyphenyl cinnamate 2-bromo-4-formyl-6-methoxyphenyl cinnamate 4-formylphenyl cinnamate (E)-4-formyl-2-methoxyphenyl 3-(3-chlorophenyl)acrylate (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(3-chlorophenyl)acrylate (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(3-chlorophenyl)acrylate (E)-4-formylphenyl 3-(3-chlorophenyl)acrylate (E)-4-formyl-2-methoxyphenyl 3-(3-bromophenyl)acrylate (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(3-bromophenyl)acrylate (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(3-bromophenyl)acrylate (E)-4-formylphenyl 3-(3-bromophenyl)acrylate (E)-4-formyl-2-methoxyphenyl 3-(3-methoxyphenyl)acrylate (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate (E)-4-formylphenyl 3-(3-methoxyphenyl)acrylate (E)-4-formyl-2-methoxyphenyl 3-(4-chlorophenyl)acrylate (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(4-chlorophenyl)acrylate (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(4-chlorophenyl)acrylate (E)-4-formylphenyl 3-(4-chlorophenyl)acrylate (E)-4-formyl-2-methoxyphenyl 3-(4-bromophenyl)acrylate (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(4-bromophenyl)acrylate (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(4-bromophenyl)acrylate (E)-4-formylphenyl 3-(4-bromophenyl)acrylate (E)-4-formyl-2-methoxyphenyl 3-(4-methoxyphenyl)acrylate (E)-2-chloro-4-formyl-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate (E)-2-bromo-4-formyl-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate (E)-4-formylphenyl 3-(4-methoxyphenyl)acrylate 4-((E)-((E)-4-(cinnamoyloxy)-3-methoxybenzylidene)amino)benzoic acid 4-((E)-((E)-3-chloro-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)benzoic acid 4-((E)-((E)-3-bromo-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)benzoic acid 4-((E)-((E)-4-(cinnamoyloxy)benzylidene)amino)benzoic acid 4-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)benzoic acid 4-((E)-((E)-3-chloro-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic acid 4-((E)-((E)-3-bromo-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic acid 4-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)benzylidene)amino)benzoic acid 4-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)benzoic acid 4-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)benzoic acid 4-((E)-((E)-3-bromo-4-((E)-3-(3-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic acid 4-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)benzylidene)amino)benzoic acid 4-((E)-((E)-3-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid 4-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid 4-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid 4-((E)-((E)-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid 4-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)benzoic acid 4-((E)-((E)-3-chloro-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic acid 4-((E)-((E)-3-bromo-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic acid 4-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)benzylidene)amino)benzoic acid 4-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)benzoic acid 4-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)benzoic acid 4-((E)-((E)-3-bromo-4-((E)-3-(4-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)benzoic acid 4-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)benzylidene)amino)benzoic acid 4-((E)-((E)-3-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid 4-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid 4-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid 4-((E)-((E)-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)benzoic acid 2-((E)-((E)-4-(cinnamoyloxy)-3-methoxybenzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-3-chloro-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-3-bromo-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-4-(cinnamoyloxy)benzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-3-chloro-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-3-bromo-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-3-bromo-4-((E)-3-(3-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-3-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-3-chloro-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-3-bromo-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-3-bromo-4-((E)-3-(4-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-3-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylbutanoic acid 2-((E)-((E)-4-(cinnamoyloxy)-3-methoxybenzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-3-chloro-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-3-bromo-4-(cinnamoyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-4-(cinnamoyloxy)benzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-3-chloro-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-3-bromo-4-((E)-3-(3-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-4-((E)-3-(3-chlorophenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-3-bromo-4-((E)-3-(3-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-4-((E)-3-(3-bromophenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-3-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-4-((E)-3-(3-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-3-chloro-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-3-bromo-4-((E)-3-(4-chlorophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-4-((E)-3-(4-chlorophenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-methoxybenzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)-3-chloro-5-methoxybenzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-3-bromo-4-((E)-3-(4-bromophenyl)acryloyloxy)-5-methoxybenzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-4-((E)-3-(4-bromophenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-3-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-3-chloro-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-3-bromo-5-methoxy-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid 2-((E)-((E)-4-((E)-3-(4-methoxyphenyl)acryloyloxy)benzylidene)amino)-3-methylpentanoic acid 4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl cinnamate 2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl cinnamate 2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl cinnamate 4-((E)-(hydroxyimino)methyl)phenyl cinnamate (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl 3-(3-chlorophenyl)acrylate (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(3-chlorophenyl)acrylate (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(3-chlorophenyl)acrylate (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(3-chlorophenyl)acrylate (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl 3-(3-bromophenyl)acrylate (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(3-bromophenyl)acrylate (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(3-bromophenyl)acrylate (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(3-bromophenyl)acrylate (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl 3-(3-methoxyphenyl)acrylate (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(3-methoxyphenyl)acrylate (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl 3-(4-chlorophenyl)acrylate (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(4-chlorophenyl)acrylate (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(4-chlorophenyl)acrylate (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(4-chlorophenyl)acrylate (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl 3-(4-bromophenyl)acrylate (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(4-bromophenyl)acrylate (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(4-bromophenyl)acrylate (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(4-bromophenyl)acrylate (E)-4-((E)-(hydroxyimino)methyl)-2-methoxyphenyl 3-(4-methoxyphenyl)acrylate (E)-2-chloro-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate (E)-2-bromo-4-((E)-(hydroxyimino)methyl)-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate (E)-4-((E)-(hydroxyimino)methyl)phenyl 3-(4-methoxyphenyl)acrylate 2-methoxy-4-((E)-ureidomethyl)phenyl cinnamate 2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl cinnamate 2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl cinnamate 4-((E)-ureidomethyl)phenyl cinnamate (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-chlorophenyl)acrylate (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-chlorophenyl)acrylate (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-chlorophenyl)acrylate (E)-4-((E)-ureidomethyl)phenyl 3-(3-chlorophenyl)acrylate (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-bromophenyl)acrylate (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-bromophenyl)acrylate (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-bromophenyl)acrylate (E)-4-((E)-ureidomethyl)phenyl 3-(3-bromophenyl)acrylate (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-methoxyphenyl)acrylate (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-methoxyphenyl)acrylate (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(3-methoxyphenyl)acrylate (E)-4-((E)-ureidomethyl)phenyl 3-(3-methoxyphenyl)acrylate (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-chlorophenyl)acrylate (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-chlorophenyl)acrylate (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-chlorophenyl)acrylate (E)-4-((E)-ureidomethyl)phenyl 3-(4-chlorophenyl)acrylate (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-bromophenyl)acrylate (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-bromophenyl)acrylate (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-bromophenyl)acrylate (E)-4-((E)-ureidomethyl)phenyl 3-(4-bromophenyl)acrylate (E)-2-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-methoxyphenyl)acrylate (E)-2-chloro-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-methoxyphenyl)acrylate (E)-2-bromo-6-methoxy-4-((E)-ureidomethyl)phenyl 3-(4-methoxyphenyl)acrylate (E)-4-((E)-ureidomethyl)phenyl 3-(4-methoxyphenyl)acrylate 4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl cinnamate 2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl cinnamate 2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl cinnamate 4-((E)-(4-hydroxyphenylimino)methyl)phenyl cinnamate (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl 3-(3-chlorophenyl)acrylate (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(3-chlorophenyl)acrylate (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(3-chlorophenyl)acrylate (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl 3-(3-chlorophenyl)acrylate (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl 3-(3-bromophenyl)acrylate (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(3-bromophenyl)acrylate (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(3-bromophenyl)acrylate (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl 3-(3-bromophenyl)acrylate (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl 3-(3-methoxyphenyl)acrylate (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl 3-(3-methoxyphenyl)acrylate (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl 3-(4-chlorophenyl)acrylate (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(4-chlorophenyl)acrylate (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(4-chlorophenyl)acrylate (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl 3-(4-chlorophenyl)acrylate (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl 3-(4-bromophenyl)acrylate (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(4-bromophenyl)acrylate (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(4-bromophenyl)acrylate (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl 3-(4-bromophenyl)acrylate (E)-4-((E)-(4-hydroxyphenylimino)methyl)-2-methoxyphenyl 3-(4-methoxyphenyl)acrylate (E)-2-chloro-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate (E)-2-bromo-4-((E)-(4-hydroxyphenylimino)methyl)-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate (E)-4-((E)-(4-hydroxyphenylimino)methyl)phenyl 3-(4-methoxyphenyl)acrylate 4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-2-methoxyphenyl cinnamate 2-chloro-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl cinnamate 2-bromo-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl cinnamate 4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)phenyl cinnamate (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-2-methoxyphenyl 3-(3-chlorophenyl)acrylate (E)-2-chloro-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(3-chlorophenyl)acrylate (E)-2-bromo-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(3-chlorophenyl)acrylate (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)phenyl 3-(3-chlorophenyl)acrylate (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-2-methoxyphenyl 3-(3-bromophenyl)acrylate (E)-2-chloro-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(3-bromophenyl)acrylate (E)-2-bromo-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(3-bromophenyl)acrylate (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)phenyl 3-(3-bromophenyl)acrylate (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-2-methoxyphenyl 3-(3-methoxyphenyl)acrylate (E)-2-chloro-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate (E)-2-bromo-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(3-methoxyphenyl)acrylate (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)phenyl 3-(3-methoxyphenyl)acrylate (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-2-methoxyphenyl 3-(4-chlorophenyl)acrylate (E)-2-chloro-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(4-chlorophenyl)acrylate (E)-2-bromo-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(4-chlorophenyl)acrylate (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)phenyl 3-(4-chlorophenyl)acrylate (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-2-methoxyphenyl 3-(4-bromophenyl)acrylate (E)-2-chloro-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(4-bromophenyl)acrylate (E)-2-bromo-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(4-bromophenyl)acrylate (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)phenyl 3-(4-bromophenyl)acrylate (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-2-methoxyphenyl 3-(4-methoxyphenyl)acrylate (E)-2-chloro-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate (E)-2-bromo-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)-6-methoxyphenyl 3-(4-methoxyphenyl)acrylate, and (E)-4-((E)-(2′-4′-dinitrophenylhydrazo)methyl)phenyl 3-(4-methoxyphenyl)acrylate.
 12. A method for the preparation of the styryl carboxylate compounds of formula (I),

or of the analog, tautomeric form, stereoisomer, polymorph, or pharmaceutically acceptable salt thereof, wherein R₁, R₂, R₃, R₄ and R₅ are predominantly hydrogens, wherein R₇ is selected from a group consisting of (i) a carbonyl group through which free amino group containing molecules can form condensates, (ii) an ethanedithiol group and (iii) a propanedithiol group, wherein each of R₆ and R₈ on ring B is selected from the group consisting of hydrogen, hydroxy, alkoxy and branched or unbranched alkyl derivatives, and wherein each of X and Y on ring B is a halogen; said method comprising the steps as shown in Scheme (I):

wherein the step from (4) to (4a) is optional depending on the required product.
 13. A method for treating a disease or physiological condition in a subject, the method comprising administering an effective amount of a compound of formula (I) as defined in claim 1 to a patient in need thereof, wherein said treatment accomplishes the result selected from the group consisting of: reducing glucose in plasma, reducing free fatty acid in plasma, reducing cholesterol in plasma, reducing triglyceride levels in plasma.
 14. A method for treating a disease or physiological condition in a subject, the method comprising administering an effective amount of a compound of formula (I) as defined in claim 1 to a patient in need thereof, wherein the disease or physiological condition is selected from the group consisting of inflammation, obesity, metabolic syndrome, an immunological disease, and an autoimmune disease.
 15. The method according to claim 14, wherein the disease is multiple sclerosis.
 16. The method according to claim 14, wherein the disease is rheumatoid arthritis.
 17. The method according to claim 14, wherein the disease or physiological condition is inflammation mediated by cyclooxygenase.
 18. The method according to claim 14, wherein the disease or physiological condition is inflammation mediated by cytokines.
 19. A method for treating a disorder associated with insulin resistance comprising administering an effective amount of a compound of formula (I) as defined in claim 1 to a patient in need thereof.
 20. The compound of claim 1 selected from the group consisting of: (4a)

S. No R7 R8 R6 R2 R3 IUPAC
 1. O OCH₃ H H H 4-formyl-2-methoxyphenyl cinnamate
 2. O OCH₃ Cl H H 2-chloro-4-formyl-6- methoxyphenyl cinnamate
 3. O OCH₃ Br H H 2-bromo-4-formyl-6- methoxyphenyl cinnamate
 4. O H H H H 4-formylphenyl cinnamate
 5. O OCH₃ H Cl H (E)-4-formyl-2- methoxyphenyl 3-(3- chlorophenyl)acrylate
 6. O OCH₃ Cl Cl H (E)-2-chloro-4-formyl-6- methoxyphenyl 3-(3- chlorophenyl)acrylate
 7. O OCH₃ Br Cl H (E)-2-bromo-4-formyl-6- methoxyphenyl 3-(3- chlorophenyl)acrylate
 8. O H H Cl H (E)-4-formylphenyl 3-(3- chlorophenyl)acrylate
 9. O OCH₃ H Br H (E)-4-formyl-2- methoxyphenyl 3-(3- bromophenyl)acrylate
 10. O OCH₃ Cl Br H (E)-2-chloro-4-formyl-6- methoxyphenyl 3-(3- bromophenyl)acrylate
 11. O OCH₃ Br Br H (E)-2-bromo-4-formyl-6- methoxyphenyl 3-(3- bromophenyl)acrylate
 12. O H H Br H (E)-4-formylphenyl 3-(3- bromophenyl)acrylate
 13. O OCH₃ H OCH₃ H (E)-4-formyl-2- methoxyphenyl 3-(3- methoxyphenyl)acrylate
 14. O OCH₃ Cl OCH₃ H (E)-2-chloro-4-formyl-6- methoxyphenyl 3-(3- methoxyphenyl)acrylate
 15. O OCH₃ Br OCH₃ H (E)-2-bromo-4-formyl-6- methoxyphenyl 3-(3- methoxyphenyl)acrylate
 16. O H H OCH₃ H (E)-4-formylphenyl 3-(3- methoxyphenyl)acrylate
 17. O OCH₃ H H Cl (E)-4-formyl-2- methoxyphenyl 3-(4- chlorophenyl)acrylate
 18. O OCH₃ Cl H Cl (E)-2-chloro-4-formyl-6- methoxyphenyl 3-(4- chlorophenyl)acrylate
 19. O OCH₃ Br H Cl (E)-2-bromo-4-formyl-6- methoxyphenyl 3-(4- chlorophenyl)acrylate
 20. O H H H Cl (E)-4-formylphenyl 3-(4- chlorophenyl)acrylate
 21. O OCH₃ H H Br (E)-4-formyl-2- methoxyphenyl 3-(4- bromophenyl)acrylate
 22. O OCH₃ Cl H Br (E)-2-chloro-4-formyl-6- methoxyphenyl 3-(4- bromophenyl)acrylate
 23. O OCH₃ Br H Br (E)-2-bromo-4-formyl-6- methoxyphenyl 3-(4- bromophenyl)acrylate
 24. O H H H Br (E)-4-formylphenyl 3-(4- bromophenyl)acrylate
 25. O OCH₃ H H OCH₃ (E)-4-formyl-2- methoxyphenyl 3-(4- methoxyphenyl)acrylate
 26. O OCH₃ Cl H OCH₃ (E)-2-chloro-4-formyl-6- methoxyphenyl 3-(4- methoxyphenyl)acrylate
 27. O OCH₃ Br H OCH₃ (E)-2-bromo-4-formyl-6- methoxyphenyl 3-(4- methoxyphenyl)acrylate
 28. O H H H OCH₃ (E)-4-formylphenyl 3-(4- methoxyphenyl)acrylate
 29.

OCH₃ H H H 4-((E)-((E)-4- (cinnamoyloxy)-3- methoxybenzylidene)amino) benzoic acid
 30.

OCH₃ Cl H H 4-((E)-((E)-3-chloro-4- (cinnamoyloxy)-5- methoxybenzylidene)amino) benzoic acid
 31.

OCH₃ Br H H 4-((E)-((E)-3-bromo-4- (cinnamoyloxy)-5- methoxybenzylidene)amino) benzoic acid
 32.

H H H H 4-((E)-((E)-4- (cinnamoyloxy)benzylidene) amino)benzoic acid
 33.

OCH₃ H Cl H 4-((E)-((E)-4-((E)-3-(3- chlorophenyl)acryloyloxy)- 3- methoxybenzylidene)amino) benzoic acid
 34.

OCH₃ Cl Cl H 4-((E)-((E)-3-chloro-4-((E)- 3-(3- chlorophenyl)acryloyloxy)- 5- methoxybenzylidene)amino) benzoic acid
 35.

OCH₃ Br Cl H 4-((E)-((E)-3-bromo-4-((E)- 3-(3- chlorophenyl)acryloyloxy)- 5- methoxybenzylidene)amino) benzoic acid
 36.

H H Cl H 4-((E)-((E)-4-((E)-3-(3- chlorophenyl)acryloyloxy) benzylidene)amino)benzoic acid
 37.

OCH₃ H Br H 4-((E)-((E)-4-((E)-3-(3- bromophenyl)acryloyloxy)- 3- methoxybenzylidene)amino) benzoic acid
 38.

OCH₃ Cl Br H 4-((E)-((E)-4-((E)-3-(3- bromophenyl)acryloyloxy)- 3-chloro-5- methoxybenzylidene)amino) benzoic acid
 39.

OCH₃ Br Br H 4-((E)-((E)-3-bromo-4-((E)- 3-(3- bromophenyl)acryloyloxy)- 5- methoxybenzylidene)amino) benzoic acid
 40.

H H Br H 4-((E)-((E)-4-((E)-3-(3- bromophenyl)acryloyloxy) benzylidene)amino)benzoic acid
 41.

OCH₃ H OCH₃ H 4-((E)-((E)-3-methoxy-4- ((E)-3-(3- methoxyphenyl)acryloyloxy) benzylidene)amino)benzoic acid
 42.

OCH₃ Cl OCH₃ H 4-((E)-((E)-3-chloro-5- methoxy-4-((E)-3-(3- methoxyphenyl)acryloyloxy) benzylidene)amino)benzoic acid
 43.

OCH₃ Br OCH₃ H 4-((E)-((E)-3-bromo-5- methoxy-4-((E)-3-(3- methoxyphenyl)acryloyloxy) benzylidene)amino)benzoic acid
 44.

H H OCH₃ H 4-((E)-((E)-4-((E)-3-(3- methoxyphenyl)acryloyloxy) benzylidene)amino)benzoic acid
 45.

OCH₃ H H Cl 4-((E)-((E)-4-((E)-3-(4- chlorophenyl)acryloyloxy)- 3- methoxybenzylidene)amino) benzoic acid
 46.

OCH₃ Cl H Cl 4-((E)-((E)-3-chloro-4-((E)- 3-(4- chlorophenyl)acryloyloxy)- 5- methoxybenzylidene)amino) benzoic acid
 47.

OCH₃ Br H Cl 4-((E)-((E)-3-bromo-4-((E)- 3-(4- chlorophenyl)acryloyloxy)- 5- methoxybenzylidene)amino) benzoic acid
 48.

H H H Cl 4-((E)-((E)-4-((E)-3-(4- chlorophenyl)acryloyloxy) benzylidene)amino)benzoic acid
 49.

OCH₃ H H Br 4-((E)-((E)-4-((E)-3-(4- bromophenyl)acryloyloxy)- 3- methoxybenzylidene)amino) benzoic acid
 50.

OCH₃ Cl H Br 4-((E)-((E)-4-((E)-3-(4- bromophenyl)acryloyloxy)- 3-chloro-5- methoxybenzylidene)amino) benzoic acid
 51.

OCH₃ Br H Br 4-((E)-((E)-3-bromo-4-((E)- 3-(4- bromophenyl)acryloyloxy)- 5- methoxybenzylidene)amino) benzoic acid
 52.

H H H Br 4-((E)-((E)-4-((E)-3-(4- bromophenyl)acryloyloxy) benzylidene)amino)benzoic acid
 53.

OCH₃ H H OCH₃ 4-((E)-((E)-3-methoxy-4- ((E)-3-(4- methoxyphenyl)acryloyloxy) benzylidene)amino)benzoic acid
 54.

OCH₃ Cl H OCH₃ 4-((E)-((E)-3-chloro-5- methoxy-4-((E)-3-(4- methoxyphenyl)acryloyloxy) benzylidene)amino)benzoic acid
 55.

OCH₃ Br H OCH₃ 4-((E)-3-((E)-3-bromo-5- methoxy-4-((E)-3-(4- methoxyphenyl)acryloyloxy) benzylidene)amino)benzoic acid
 56.

H H H OCH₃ 4-((E)-((E)-4-((E)-3-(4- methoxyphenyl)acryloyloxy) benzylidene)amino)benzoic acid
 57.

OCH₃ H H H 2-((E)-((E)-4- (cinnamoyloxy)-3- methoxybenzylidene)amino)- 3-methylbutanoic acid
 58.

OCH₃ Cl H H 2-((E)-((E)-3-chloro-4- (cinnamoyloxy)-5- methoxybenzylidene)amino)- 3-methylbutanoic acid
 59.

OCH₃ Br H H 2-((E)-((E)-3-bromo-4- (cinnamoyloxy)-5- methoxybenzylidene)amino)- 3-methylbutanoic acid
 60.

H H H H 2-((E)-((E)-4- (cinnamoyloxy)benzylidene) amino)-3-methylbutanoic acid
 61.

OCH₃ H Cl H 2-((E)-((E)-4-((E)-3-(3- chlorophenyl)acryloyloxy)- 3- methoxybenzylidene)amino)- 3-methylbutanoic acid
 62.

OCH₃ Cl Cl H 2-((E)-((E)-3-chloro-4-((E)- 3-(3- chlorophenyl)acryloyloxy)- 5- methoxybenzylidene)amino)- 3-methylbutanoic acid
 63.

OCH₃ Br Cl H 2-((E)-((E)-3-bromo-4-((E)- 3-(3- chlorophenyl)acryloyloxy)- 5- methoxybenzylidene)amino)- 3-methylbutanoic acid
 64.

H H Cl H 2-((E)-((E)-4-((E)-3-(3- chlorophenyl)acryloyloxy) benzylidene)amino)-3- methylbutanoic acid
 65.

OCH₃ H Br H 2-((E)-((E)-4-((E)-3-(3- bromophenyl)acryloyloxy)- 3- methoxybenzylidene)amino)- 3-methylbutanoic acid
 66.

OCH₃ Cl Br H 2-((E)-((E)-4-((E)-3-(3- bromophenyl)acryloyloxy)- 3-chloro-5- methoxybenzylidene)amino)- 3-methylbutanoic acid
 67.

OCH₃ Br Br H 2-((E)-((E)-3-bromo-4-((E)- 3-(3- bromophenyl)acryloyloxy)- 5- methoxybenzylidene)amino)- 3-methylbutanoic acid
 68.

H H Br H 2-((E)-((E)-4-((E)-3-(3- bromophenyl)acryloyloxy) benzylidene)amino)-3- methylbutanoic acid
 69.

OCH₃ H OCH₃ H 2-((E)-((E)-3-methoxy-4- ((E)-3-(3- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylbutanoic acid
 70.

OCH₃ Cl OCH₃ H 2-((E)-((E)-3-chloro-5- methoxy-4-((E)-3-(3- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylbutanoic acid
 71.

OCH₃ Br OCH₃ H 2-((E)-((E)-3-bromo-5- methoxy-4-((E)-3-(3- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylbutanoic acid
 72.

H H OCH₃ H 2-((E)-((E)-4-((E)-3-(3- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylbutanoic acid
 73.

OCH₃ H H Cl 2-((E)-((E)-4-((E)-3-(4- chlorophenyl)acryloyloxy)- 3- methoxybenylidene)amino)- 3-methylbutanoic acid
 74.

OCH₃ Cl H Cl 2-((E)-((E)-3-chloro-4-((E)- 3-(4- chlorophenyl)acryloyloxy)- 5- methoxybenzylidene)amino)- 3-methylbutanoic acid
 75.

OCH₃ Br H Cl 2-((E)-((E)-3-bromo-4-((E)- 3-(4- chlorophenyl)acryloyloxy)- 5- methoxybenzylidene)amino)- 3-methylbutanoic acid
 76.

H H H Cl 2-((E)-((E)-4-((E)-3-(4- chlorophenyl)acryloyloxy) benzylidene)amino)-3- methylbutanoic acid
 77.

OCH₃ H H Br 2-((E)-((E)-4-((E)-3-(4- bromophenyl)acryloyloxy)- 3- methoxybenzylidene)amino)- 3-methylbutanoic acid
 78.

OCH₃ Cl H Br 2-((E)-((E)-4-((E)-3-(4- bromophenyl)acryloyloxy)- 3-chloro-5- methoxybenzylidene)amino)- 3-methylbutanoic acid
 79.

OCH₃ Br H Br 2-((E)-((E)-3-bromo-4-((E)- 3-(4- bromophenyl)acryloyloxy)- 5- methoxybenzylidene)amino)- 3-methylbutanoic acid
 80.

H H H Br 2-((E)-((E)-4-((E)-3-(4- bromophenyl)acryloyloxy) benzylidene)amino)-3- methylbutanoic acid
 81.

OCH₃ H H OCH₃ 2-((E)-((E)-3-methoxy-4- ((E)-3-(4- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylbutanoic acid
 82.

OCH₃ Cl H OCH₃ 2-((E)-((E)-3-chloro-5- methoxy-4-((E)-3-(4- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylbutanoic acid
 83.

OCH₃ Br H OCH₃ 2-((E)-((E)-3-bromo-5- methoxy-4-((E)-3-(4- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylbutanoic acid
 84.

H H H OCH₃ 2-((E)-((E)-4-((E)-3-(4- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylbutanoic acid
 85.

OCH₃ H H H 2-((E)-((E)-4- (cinnamoyloxy)-3- methoxybenzylidene)amino)- 3-methylpentanoic acid
 86.

OCH₃ Cl H H 2-((E)-((E)-3-chloro-4- (cinnamoyloxy)-5- methoxybenzylidene)amino)- 3-methylpentanoic acid
 87.

OCH₃ Br H H 2-((E)-((E)-3-bromo-4- (cinnamoyloxy)-5- methoxybenzylidene)amino)- 3-methylpentanoic acid
 88.

H H H H 2-((E)-((E)-4- (cinnamoyloxy)benzylidene) amino)-3-methylpentanoic acid
 89.

OCH₃ H Cl H 2-((E)-((E)-4-((E)-3-(3- chlorophenyl)acryloyloxy)- 3- methoxybenzylidene)amino)- 3-methylpentanoic acid
 90.

OCH₃ Cl Cl H 2-((E)-((E)-3-chloro-4-((E)- 3-(3- chlorophenyl)acryloyloxy)- 5- methoxybenzylidene)amino)- 3-methylpentanoic acid
 91.

OCH₃ Br Cl H 2-((E)-((E)-3-bromo-4-((E)- 3-(3- chlorophenyl)acryloyloxy)- 5- methoxybenzylidene)amino)- 3-methylpentanoic acid
 92.

H H Cl H 2-((E)-((E)-4-((E)-3-(3- chlorophenyl)acryloyloxy) benzylidene)amino)-3- methylpentanoic acid
 93.

OCH₃ H Br H 2-((E)-((E)-4-((E)-3-(3- bromophenyl)acryloyloxy)- 3- methoxybenzylidene)amino)- 3-methylpentanoic acid
 94.

OCH₃ Cl Br H 2-((E)-((E)-4-((E)-3-(3- bromophenyl)acryloyloxy)- 3-chloro-5- methoxybenzylidene)amino)- 3-methylpentanoic acid
 95.

OCH₃ Br Br H 2-((E)-((E)-3-bromo-4-((E)- 3-(3- bromophenyl)acryloyloxy)- 5- methoxybenzylidene)amino)- 3-methylpentanoic acid
 96.

H H Br H 2-((E)-((E)-4-((E)-3-(3- bromophenyl)acryloyloxy) benzylidene)amino)-3- methylpentanoic acid
 97.

OCH₃ H OCH₃ H 2-((E)-((E)-3-methoxy-4- ((E)-3-(3- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylpentanoic acid
 98.

OCH₃ Cl OCH₃ H 2-((E)-((E)-3-chloro-5- methoxy-4-((E)-3-(3- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylpentanoic acid
 99.

OCH₃ Br OCH₃ H 2-((E)-((E)-3-bromo-5- methoxy-4-((E)-3-(3- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylpentanoic acid
 100.

H H OCH₃ H 2-((E)-((E)-4-((E)-3-(3- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylpentanoic acid
 101.

OCH₃ H H Cl 2-((E)-((E)-4-((E)-3-(4- chlorophenyl)acryloyloxy)- 3- methoxybenzylidene)amino)- 3-methylpentanoic acid
 102.

OCH₃ Cl H Cl 2-((E)-((E)-3-chloro-4-((E)- 3-(4- chlorophenyl)acryloyloxy)- 5- methoxybenzylidene)amino)- 3-methylpentanoic acid
 103.

OCH₃ Br H Cl 2-((E)-((E)-3-bromo-4-((E)- 3-(4- chlorophenyl)acryloyloxy)- 5- methoxybenzylidene)amino)- 3-methylpentanoic acid
 104.

H H H Cl 2-((E)-((E)-4-((E)-3-(4- chlorophenyl)acryloyloxy) benzylidene)amino)-3- methylpentanoic acid
 105.

OCH₃ H H Br 2-((E)-((E)-4-((E)-3-(4- bromophenyl)acryloyloxy)- 3- methoxybenzylidene)amino)- 3-methylpentanoic acid
 106.

OCH₃ Cl H Br 2-((E)-((E)-4-((E)-3-(4- bromophenyl)acryloyloxy)- 3-choro-5- methoxybenzylidene)amino)- 3-methylpentanoic acid
 107.

OCH₃ Br H Br 2-((E)-((E)-3-bromo-4-((E)- 3-(4- bromophenyl)acryloyloxy)- 5- methoxybenzylidene)amino)- 3-methylpentanoic acid
 108.

H H H Br 2-((E)-((E)-4-((E)-3-(4- bromophenyl)acryloyloxy) benzylidene)amino)-3- methylpentanoic acid
 109.

OCH₃ H H OCH₃ 2-((E)-((E)-3-methoxy-4- ((E)-3-(4- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylpentanoic acid
 110.

OCH₃ Cl H OCH₃ 2-((E)-((E)-3-chloro-5- methoxy-4-((E)-3-(4- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylpentanoic acid
 111.

OCH₃ Br H OCH₃ 2-((E)-((E)-3-bromo-5- methoxy-4-((E)-3-(4- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylpentanoic acid
 112.

H H H OCH₃ 2-((E)-((E)-4-((E)-3-(4- methoxyphenyl)acryloyloxy) benzylidene)amino)-3- methylpentanoic acid
 113. NOH OCH₃ H H H 4-((E)- (hydroxyimino)methyl)-2- methoxyphenyl cinnamate
 114. NOH OCH₃ Cl H H 2-chloro-4-((E)- (hydroxyimino)methyl)-6- methoxyphenyl cinnamate
 115. NOH OCH₃ Br H H 2-bromo-4-((E)- (hydroxyimino)methyl)-6- methoxyphenyl cinnamate
 116. NOH H H H H 4-((E)- (hydroxyimino)methyl) phenyl cinnamate
 117. NOH OCH₃ H Cl H (E)-4-((E)- (hydroxyimino)methyl)-2- methoxyphenyl 3-(3- chlorophenyl)acrylate
 118. NOH OCH₃ Cl Cl H (E)-2-chloro-4-((E)- (hydroxyimino)methyl)-6- methoxyphenyl 3-(3- chlorophenyl)acrylate
 119. NOH OCH₃ Br Cl H (E)-2-bromo-4-((E)- (hydroxyimino)methyl)-6- methoxyphenyl 3-(3- chlorophenyl)acrylate
 120. NOH H H Cl H (E)-4-((E)- (hydroxyimino)methyl) phenyl 3-(3-chlorophenyl)acrylate
 121. NOH OCH₃ H Br H (E)-4-((E)- (hydroxyimino)methyl)-2- methoxyphenyl 3-(3- bromophenyl)acrylate
 122. NOH OCH₃ Cl Br H (E)-2-chloro-4-((E)- (hydroxyimino)methyl)-6- methoxyphenyl 3-(3- bromophenyl)acrylate
 123. NOH OCH₃ Br Br H (E)-2-bromo-4-((E)- (hydroxyimino)methyl)-6- methoxyphenyl 3-(3- bromophenyl)acrylate
 124. NOH H H Br H (E)-4-((E)- (hydroxyimino)methyl) phenyl 3-(3-bromophenyl)acrylate
 125. NOH OCH₃ H OCH₃ H (E)-4-((E)- (hydroxyimino)methyl)-2- methoxyphenyl 3-(3- methoxyphenyl)acrylate
 126. NOH OCH₃ Cl OCH₃ H (E)-2-chloro-4-((E)- (hydroxyimino)methyl)-6- methoxyphenyl 3-(3- methoxyphenyl)acrylate
 127. NOH OCH₃ Br OCH₃ H (E)-2-bromo-4-((E)- (hydroxyimino)methyl)-6- methoxyphenyl 3-(3- methoxyphenyl)acrylate
 128. NOH H H OCH₃ H (E)-4-((E)- (hydroxyimino)methyl) phenyl 3-(3- methoxyphenyl)acrylate
 129. NOH OCH₃ H H Cl (E)-4-((E)- (hydroxyimino)methyl)-2- methoxyphenyl 3-(4- chlorophenyl)acrylate
 130. NOH OCH₃ Cl H Cl (E)-2-chloro-4-((E)- (hydroxyimino)methyl)-6- methoxyphenyl 3-(4- chlorophenyl)acrylate
 131. NOH OCH₃ Br H Cl (E)-2-bromo-4-((E)- (hydroxyimino)methyl)-6- methoxyphenyl 3-(4- chlorophenyl)acrylate
 132. NOH H H H Cl (E)-4-((E)- (hydroxyimino)methyl) phenyl 3-(4-chlorophenyl)acrylate
 133. NOH OCH₃ H H Br (E)-4-((E)- (hydroxyimino)methyl)-2- methoxyphenyl 3-(4- bromophenyl)acrylate
 134. NOH OCH₃ Cl H Br (E)-2-chloro-4-((E)- (hydroxyimino)methyl)-6- methoxyphenyl 3-(4- bromophenyl)acrylate
 135. NOH OCH₃ Br H Br (E)-2-bromo-4-((E)- (hydroxyimino)methyl)-6- methoxyphenyl 3-(4- bromophenyl)acrylate
 136. NOH H H H Br (E)-4-((E)- (hydroxyimino)methyl)phenyl 3-(4-bromophenyl)acrylate
 137. NOH OCH₃ H H OCH₃ (E)-4-((E)- (hydroxyimino)methyl)-2- methoxyphenyl 3-(4- methoxyphenyl)acrylate
 138. NOH OCH₃ Cl H OCH₃ (E)-2-chloro-4-((E)- (hydroxyimino)methyl)-6- methoxyphenyl 3-(4- methoxyphenyl)acrylate
 139. NOH OCH₃ Br H OCH₃ (E)-2-bromo-2-((E)- (hydroxyimino)methyl)-6- methoxyphenyl 3-(4- methoxyphenyl)acrylate
 140. NOH H H H OCH₃ (E)-4-((E)- (hydroxyimino)methyl)phenyl 3-(4- methoxyphenyl)acrylate
 141. NCONH₂ OCH₃ H H H 2-methoxy-4-((E)- ureidomethyl)phenyl cinnamate
 142. NCONH₂ OCH₃ Cl H H 2-chloro-6-methoxy-4-((E)- ureidomethyl)phenyl cinnamate
 143. NCONH₂ OCH₃ Br H H 2-bromo-6-methoxy-4-((E)- ureidomethyl)phenyl cinnamate
 144. NCONH₂ H H H H 4-((E)-ureidomethyl)phenyl cinnamate
 145. NCONH₂ OCH₃ H Cl H (E)-2-methoxy-4-((E)- ureidomethyl)phenyl 3-(3- chlorophenyl)acrylate
 146. NCONH₂ OCH₃ Cl Cl H (E)-2-chloro-6-methoxy-4- ((E)-ureidomethyl)phenyl 3- (3-chlorophenyl)acrylate
 147. NCONH₂ OCH₃ Br Cl H (E)-2-bromo-6-methoxy-4- ((E)-ureidomethyl)phenyl 3- (3-chlorophenyl)acrylate
 148. NCONH₂ H H Cl H (E)-4-((E)- ureidomethyl)phenyl 3-(3- chlorophenyl)acrylate
 149. NCONH₂ OCH₃ H Br H (E)-2-methoxy-4-((E)- ureidomethyl)phenyl 3-(3- bromophenyl)acrylate
 150. NCONH₂ OCH₃ Cl Br H (E)-2-chloro-6-methoxy-4- ((E)-ureidomethyl)phenyl 3- (3-bromophenyl)acrylate
 151. NCONH₂ OCH₃ Br Br H (E)-2-bromo-6-methoxy-4- ((E)-ureidomethyl)phenyl 3- (3-bromophenyl)acrylate
 152. NCONH₂ H H Br H (E)-4-((E)- ureidomethyl)phenyl 3-(3- bromophenyl)acrylate
 153. NCONH₂ OCH₃ H OCH₃ H (E)-2-methoxy-4-((E)- ureidomethyl)phenyl 3-(3- methoxyphenyl)acrylate
 154. NCONH₂ OCH₃ Cl OCH₃ H (E)-2-chloro-6-methoxy-4- ((E)-ureidomethyl)phenyl 3- (3-methoxyphenyl)acrylate
 155. NCONH₂ OCH₃ Br OCH₃ H (E)-2-bromo-6-methoxy-4- ((E)-ureidomethyl)phenyl 3- (3-methoxyphenyl)acrylate
 156. NCONH₂ H H OCH₃ H (E)-4-((E)- ureidomethyl)phenyl 3-(3- methoxyphenyl)acrylate
 157. NCONH₂ OCH₃ H H Cl (E)-2-methoxy-4-((E)- ureidomethyl)phenyl 3-(4- chlorophenyl)acrylate
 158. NCONH₂ OCH₃ Cl H Cl (E)-2-chloro-6-methoxy-4- ((E)-ureidomethyl)phenyl 3- (4-chlorophenyl)acrylate
 159. NCONH₂ OCH₃ Br H Cl (E)-2-bromo-6-methoxy-4- ((E)-ureidomethyl)phenyl 3- (4-chlorophenyl)acrylate
 160. NCONH₂ H H H Cl (E)-4-((E)- ureidomethyl)phenyl 3-(4- chlorophenyl)acrylate
 161. NCONH₂ OCH₃ H H Br (E)-2-methoxy-4-((E)- ureidomethyl)phenyl 3-(4- bromophenyl)acrylate
 162. NCONH₂ OCH₃ Cl H Br (E)-2-chloro-6-methoxy-4- ((E)-ureidomethyl)phenyl 3- (4-bromophenyl)acrylate
 163. NCONH₂ OCH₃ Br H Br (E)-2-bromo-6-methoxy-4- ((E)-ureidomethyl)phenyl 3- (4-bromophenyl)acrylate
 164. NCONH₂ H H H Br (E)-4-((E)- ureidomethyl)phenyl 3-(4- bromophenyl)acrylate
 165. NCONH₂ OCH₃ H H OCH₃ (E)-2-methoxy-4-((E)- ureidomethyl)phenyl 3-(4- methoxyphenyl)acrylate
 166. NCONH₂ OCH₃ Cl H OCH₃ (E)-2-chloro-6-methoxy-4- ((E)-ureidomethyl)phenyl 3- (4-methoxyphenyl)acrylate
 167. NCONH₂ OCH₃ Br H OCH₃ (E)-2-bromo-6-methoxy-4- ((E)-ureidomethyl)phenyl 3- (4-methoxyphenyl)acrylate
 168. NCONH₂ H H H OCH₃ (E)-4-((E)- ureidomethyl)phenyl 3-(4- methoxyphenyl)acrylate
 169.

OCH₃ H H H 4-((E)-(4- hydroxyphenylimino)methyl)- 2-methoxyphenyl cinnamate
 170.

OCH₃ Cl H H 2-chloro-4-((E)-(4- hydroxyphenylimino)methyl)- 6-methoxyphenyl cinnamate
 171.

OCH₃ Br H H 2-bromo-4-((E)-(4- hydroxyphenylimino)methyl)- 6-methoxyphenyl cinnamate
 172.

H H H H 4-((E)-(4- hydroxyphenylimino)methyl) phenyl cinnamate
 173.

OCH₃ H Cl H (E)-4-((E)-4- hydroxyphenylimino)methyl)- 2-methoxyphenyl 3-(3- chlorophenyl)acrylate
 174.

OCH₃ Cl Cl H (E)-2-chloro-4-((E)-(4- hydroxyphenylimino)methyl)- 6-methoxyphenyl 3-(3- chlorophenyl)acrylate
 175.

OCH₃ Br Cl H (E)-2-bromo-4-((E)-(4- hydroxyphenylimino)methyl)- 6-methoxyphenyl 3-(3- chlorophenyl)acrylate
 176.

H H Cl H (E)-((E)-(4- hydroxyphenylimino)methyl) phenyl 3-(3- chlorophenyl)acrylate
 177.

OCH₃ H Br H (E)-4-((E)-(4- hydroxyphenylimino)methyl)- 2-methoxyphenyl 3-(3- bromophenyl)acrylate
 178.

OCH₃ Cl Br H (E)-2-chloro-4-((E)-(4- hydroxyphenylimino)methyl)- 6-methoxyphenyl 3-(3- bromophenyl)acrylate
 179.

OCH₃ Br Br H (E)-2-bromo-4-((E)-(4- hydroxyphenylimino)methyl)- 6-methoxyphenyl 3-(3- bromophenyl)acrylate
 180.

H H Br H (E)-4-((E)-(4- hydroxyphenylimino)methyl) phenyl 3-(3- bromophenyl)acrylate
 181.

OCH₃ H OCH₃ H (E)-4-((E)-(4- hydroxyphenylimino)methyl)- 2-methoxyphenyl 3-(3- methoxyphenyl)acrylate
 182.

OCH₃ Cl OCH₃ H (E)-2-chloro-4-((E)-(4- hydroxyphenylimino)methyl)- 6-methoxyphenyl 3-(3- methoxyphenyl)acrylate
 183.

OCH₃ Br OCH₃ H (E)-2-bromo-4-((E)-(4- hydroxyphenylimino)methyl)- 6-methoxyphenyl 3-(3- methoxyphenyl)acrylate
 184.

H H OCH₃ H (E)-4-((E)-(4- hydroxyphenylimino)methyl)- phenyl 3-(3- methoxyphenyl)acrylate
 185.

OCH₃ H H Cl (E)-4-((E)-(4- hydroxyphenylimino)methyl)- 2-methoxyphenyl 3-(4- chlorophenyl)acrylate
 186.

OCH₃ Cl H Cl (E)-2-chloro-4-((E)-(4- hydroxyphenylimino)methyl)- 6-methoxyphenyl 3-(4- chlorophenyl)acrylate
 187.

OCH₃ Br H Cl (E)-2-bromo-4-((E)-(4- hydroxyphenylimino)methyl)- 6-methoxyphenyl 3-(4- chlorophenyl)acrylate
 188.

H H H Cl (E)-4-((E)-(4- hydroxyphenylimino)methyl) phenyl 3-(4- chlorophenyl)acrylate
 189.

OCH₃ H H Br (E)-4-((E)-(4- hydroxyphenylimino)methyl)- 2-methoxyphenyl 3-(4- bromophenyl)acrylate
 190.

OCH₃ Cl H Br (E)-2-chloro-4-((E)-(4- hydroxyphenylimino)methyl)- 6-methoxyphenyl 3-(4- bromophenyl)acrylate
 191.

OCH₃ Br H Br (E)-2-bromo-4-((E)-(4- hydroxyphenylimino)methyl)- 6-methoxyphenyl 3-(4- bromophenyl)acrylate
 192.

H H H Br (E)-4-((E)-(4- hydroxyphenylimino)methyl) phenyl 3-(4- bromophenyl)acrylate
 193.

OCH₃ H H OCH₃ (E)-4-((E)-(4- hydroxyphenylimino)methyl)- 2-methoxyphenyl 3-(4- methoxyphenyl)acrylate
 194.

OCH₃ Cl H OCH₃ (E)-2-chloro-4-((E)-(4- hydroxyphenylimino)methyl)- 6-methoxyphenyl 3-(4- methoxyphenyl)acrylate
 195.

OCH₃ Br H OCH₃ (E)-2-bromo-4-((E)-(4- hydroxyphenylimino)methyl)- 6-methoxyphenyl 3-(4- methoxyphenyl)acrylate
 196.

H H H OCH₃ (E)-4-((E)-(4- hydroxyphenylimino)methyl) phenyl 3-(4- methoxyphenyl)acrylate
 197.

OCH₃ H H H 4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 2-methoxyphenyl cinnamate
 198.

OCH₃ Cl H H 2-chloro-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 6-methoxyphenyl cinnamate
 199.

OCH₃ Br H H 2-bromo-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 6-methoxyphenyl cinnamate
 200.

H H H H 4-((E)-(2′-4′- dinitrophenylhydrazo)methyl) phenyl cinnamate
 201.

OCH₃ H Cl H (E)-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 2-methoxyphenyl 3-(3- chlorophenyl)acrylate
 202.

OCH₃ Cl Cl H (E)-2-chloro-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 6-methoxyphenyl 3-(3- chlorophenyl)acrylate
 203.

OCH₃ Br Cl H (E)-2-bromo-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 6-methoxyphenyl 3-(3- chlorophenyl)acrylate
 204.

H H Cl H (E)-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl) phenyl 3-(3- chlorophenyl)acrylate
 205.

OCH₃ H Br H (E)-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 2-methoxyphenyl 3-(3- bromophenyl)acrylate
 206.

OCH₃ Cl Br H (E)-2-chloro-4-((E)-(2′-4′- dinitrophenyhydrazo)methyl)- 6-methoxyphenyl 3-(3- bromophenyl)acrylate
 207.

OCH₃ Br Br H (E)-2-bromo-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 6-methoxyphenyl 3-(3- bromophenyl)acrylate
 208.

H H Br H (E)-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl) phenyl 3-(3- bromophenyl)acrylate
 209.

OCH₃ H OCH₃ H (E)-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 2-methoxyphenyl 3-(3- methoxyphenyl)acrylate
 210.

OCH₃ Cl OCH₃ H (E)-2-chloro-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 6-methoxyphenyl 3-(3- methoxyphenyl)acrylate
 211.

OCH₃ Br OCH₃ H (E)-2-bromo-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 6-methoxyphenyl 3-(3- methoxyphenyl)acrylate
 212.

H H OCH₃ H (E)-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl) phenyl 3-(3- methoxyphenyl)acrylate
 213.

OCH₃ H H Cl (E)-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 2-methoxyphenyl 3-(4- chlorophenyl)acrylate
 214.

OCH₃ Cl H Cl (E)-2-chloro-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 6-methoxyphenyl 3-(4- chlorophenyl)acrylate
 215.

OCH₃ Br H Cl (E)-2-bromo-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 6-methoxyphenyl 3-(4- chlorophenyl)acrylate
 216.

H H H Cl (E)-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl) phenyl 3-(4- chlorophenyl)acrylate
 217.

OCH₃ H H Br (E)-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 2-methoxyphenyl 3-(4- bromophenyl)acrylate
 218.

OCH₃ Cl H Br (E)-2-chloro-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 6-methoxyphenyl 3-(4- bromophenyl)acrylate
 219.

OCH₃ Br H Br (E)-2-bromo-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 6-methoxyphenyl 3-(4- bromophenyl)acrylate
 220.

H H H Br (E)-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl) phenyl 3-(4- bromophenyl)acrylate
 221.

OCH₃ H H OCH₃ (E)-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 2-methoxyphenyl 3-(4- methoxyphenyl)acrylate
 222.

OCH₃ Cl H OCH₃ (E)-2-chloro-4-((E)-(2′-4′ dinitrophenylhydrazo)methyl)- 6-methoxyphenyl 3-(4- methoxyphenyl)acrylate
 223.

OCH₃ Br H OCH₃ (E)-2-bromo-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl)- 6-methoxyphenyl 3-(4- methoxyphenyl)acrylate
 224.

H H H OCH₃ (E)-4-((E)-(2′-4′- dinitrophenylhydrazo)methyl) phenyl 3-(4- methoxyphenyl)acrylate 